


Tiny Vessels

by ArchOfImagine



Series: Tiny Lessons [1]
Category: Supernatural
Genre: Alternate Universe - Domestic, F/M, Light BDSM, Light Dom/sub, M/M, Married Castiel, Nanny Dean, Smut, Writer Castiel, Young Dean Winchester, top/bottom roles will be clearly labeled before chapters involving sex
Language: English
Status: Completed
Published: 2014-10-28
Updated: 2014-12-23
Packaged: 2018-02-22 23:44:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 25
Words: 43,621
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2526044
Author URL: https://archiveofourown.org/users/ArchOfImagine/pseuds/ArchOfImagine
Summary: <blockquote class="userstuff">
              <p>It was Dean's last interview. His last chance to find a job in sunny California. If it didn't go well, he would have to go back to life in Kansas. But when you're applying for a live-in nanny position, it isn't just about pleasing the 'boss'... it's about pleasing the boss' kid.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Special thanks to [hufflecas](http://hufflecas.tumblr.com) for being my awesome beta/soundboard/muse. 
> 
> Title is from a Death Cab for Cutie song of the same name. No relevance, I just thought it worked. All 'toddler tips' are taken from [Honest Toddler](https://twitter.com/HonestToddler) over on twitter.
> 
> I know it's crazy to start a WIP when I literally have 6 big bang stories in the works, but this idea has been around for months and last night I had a dream that fit into the verse and I just couldn't stop myself. So kudos and good vibes will keep the muse happy and updates flying!
> 
> Also: I have purposefully been vague about tagging. I don't want to ruin the whole story now by laying out what will happen involving future aspects. There WILL NOT be character death, don't worry. This story will be mostly fluffy smutty goodness. If I feel anything will be particularly triggering, I will tag that chapter.

_Toddler Tip: A fun alternative to eating is to just crumble the food in your hand. Try it._  


\---

When Dean told his mother that he wanted to move to southern California, it really pushed her ‘follow your dreams’ mentality to the limit. She supported him, of course, but that didn’t mean she kept her opinion of how crazy she thought he was to herself. He was nineteen, he didn’t have a job or a place to move to, and his only real source of income was a few modest student loans so that he could go to school online.

But none of that mattered. He had outgrown Kansas and needed to get away from the podunk little town he had grown up in. Even if it meant leaving his mom and brother, it would be worth it to live by the ocean. 

Two months after arriving in Los Angeles, he was staring at his last two hundred dollars. He was at a crossroads. The money before him was just enough to pay for gas to get back home, or he could stick it out and continue knocking on every door until he found work. _Damn it._ Dean didn’t want to go home. Two months had been enough to show him that he loved California, and he wasn’t ready to give up and go back to the farm.

“Five more interviews,” he mumbled, scoping out more advertisements in the paper. “Two weeks. Five interviews. If nothing comes of it… back home.”

\---

By the time the fifth interview rolled around, Dean was losing hope. He had tried construction companies, car repair shops, and even one _nevergonnamentionitagain_ moment at Sears. 

He was on his last shot at staying. And he hated to admit it, but he was depending on old skills that he thought he’d never use again.

Dressed in a button down shirt and black slacks, Dean walked into the non-descript office building and followed the directions he’d been given to the fifth floor. Stepping off the elevator, he stared at the glass door in front of him.

It had a brass plaque in the middle of it that read: _Novak Editing and Publishing_. Considering that neither of those things had anything to do with the job that Dean had applied for, he was more than a little weary and confused. 

It was interview number five, though. His last option.

Stepping inside, he forced a smile at the older woman sitting behind the receptionist’s desk. “Hi, I’m Dean Winchester. I’m here to—”

“Right!” She gave him a brief glance before motioning to the door on her right. “Go in there and have a seat on the couch. Mr. Novak will be with you shortly.”

The room he stepped into, laid out with a couch on one wall and two chairs along the other, definitely didn’t help his feelings of dread. 

If someone walked in with a video camera he was _out of there_.

He sat on the couch, nervously tapping his fingers along his knee, for ten minutes, before the door finally opened again. 

A tall man with dark hair entered. He looked more than a little frazzled and unkempt. Instead of a suit, like Dean had expected, the guy was wearing a black t-shirt and dark wash jeans. He carried a cup of coffee and a folder, and used his foot to close the door behind him. 

“Sorry I’m late, Mr. Winchester.” He glanced up at Dean for a brief moment, before sitting down in one of the chairs across from the couch. “It’s been a busy day. How are you doing?”

Dean remained silent for a long moment as he stared at the guy. His eyes moved down the length of the other man’s body and stopped at the floor where his _bare feet_ rested. _Well then._ “I’m good,” he finally managed. Looking back up, he noticed that the man—Mr. Novak—was watching him with a raised eyebrow. _Right, interview._ He expected more than two words. “I’ve been sitting here praying that this wasn’t a set up for one of those ‘couch confessions’ pornos.”

_Shit._ Dean felt like slapping himself. Since when did he think it was okay to mention porn at a fucking job interview? 

Before he could apologize for the lack of brainwaves and nervous statements, Mr. Novak let out a soft chuckle. “I suppose it does look kind of suspicious. I assure you, though, I’m not making a pornagraphic movie. I really am just looking for a reliable live-in nanny.”

\---

Despite Mr. Novak’s fears that he wouldn’t be good with children, the interview seemed to go well. Dean explained his experience—how he had helped his mother raise his baby brother after his father’s death, and then continued helping her when she had opened an in-home daycare. He knew how to handle children of all ages, and just wanted reliable work and time to spend enjoying California while he finished school.

Mr. Novak didn’t promise him employment, but he did invite Dean to a second interview at his home… where he would have to pass the ‘hard part’ of the hiring process. _Meeting the kid._

Two days later, Dean drove his dad’s old Impala to a nice neighborhood in West Hollywood. They wasn’t the fanciest homes in Los Angeles, but it wasn’t exactly modest, either. He scanned the house numbers, driving slowly down the street until he found the two story house he’d been looking for. 

“Here goes nothing,” he mumbled, shutting off the car and climbing out. 

At the front door, he knocked instead of ringing the bell—knowing that kids liked to take random naps and nothing made a parent angrier than a bell waking a sleeping kid.

He was just about ready to knock again when the door opened. Mr. Novak stood on the other side, wearing jeans like at the first interview… but no shirt. Dean’s eyes were quickly drawn to the older man’s left leg, where a small boy with light blonde hair had wrapped himself.

“Dean, good to see you again.” Mr. Novak shook his hand, before motioning down his body. “This is Boston. Bo, say hi.” 

The boy buried his face in his father’s pants, causing Dean to smile. Sam had been shy like that when he was little. “Hey, pal, I’m Dean.”

Mr. Novak stepped aside and motioned Dean in. The place was nice, clean, and modern… but it was definitely obvious that a three-year-old lived there. Toys and books and sippy cups seemed to be scattered everywhere. 

“I’m sorry for the mess. My wife is out of town on a press tour and, well—Bo and I aren’t the cleanest.”

“It’s fine, Mr. Novak.” Dean smiled, looking at the man quickly but avoiding the wide expanse of tan skin that could be seen thanks to his bare chest. It was much easier to look around the house and at the kid. 

“Please, no formalities here. Castiel or Cas is fine.” Sensing the awkward tension, Mr. Nov—er _Castiel_ glanced down and seemed to realize he was a bit underdressed. “Shi... itake mushrooms. Sorry, Dean, I was making lunch and there was a bit of a spaghetti-o fiasco. Let me just go grab a clean shirt.” He turned to walk towards the stairs, but stopped when he noticed Boston still clinging to his leg. “Stay here, Bo. Why don’t you show Dean your books?”

The boy let go of his father, but remained sitting on the floor instead of going near Dean. _Definitely shy._ Since the whole point of the second interview was to prove that he could get along with Boston, Dean knew that making the kid like him was going to be his easiest path to employment.

Leaving Bo by the stairs, he walked into the nearby family room area and sat down in the middle of the floor amongst a scattering of toys. “Hmm. What should I play with first?” There were quite a few ‘learning friendly’ toys, but Dean immediately skipped over them when he spotted a set of monster trucks. “Oh sweet, I used to love these things!”

He could sense Boston moving closer, but ignored the boy as he set up a makeshift demolition track using various other toys. Once he had it set up, he rolled one of the monster trucks closer with a grin.

In his cheesiest announcer voice, he spoke up, “This Sunday, Sunday, Sunday, live at the Novak Arena it’s…. BIGFOOT!” He mimicked a crowd of screaming fans. 

Across the room, the tiniest of giggles could be heard as Bo peered out from around the side of the couch to watch Dean.

“And challenging Bigfoot?” He continued. “None other than…” Dean looked up, catching Bo’s eyes and grinning. “BOSTON the DESTROYER!”

Hearing his name, Boston giggled again and slowly stepped forward. “Can I play?” the boy asked, his voice soft.

“Of course, Mr. Destroyer Man. Which one do you want to be?”

A few minutes later, Dean glanced up from playing with Bo to see Mr. Novak standing at the edge of the room watching them. His arms were crossed over a blue polo shirt and he was smiling approvingly. “You’re hired, Dean. When can you move in?”


	2. Chapter 2

_Toddler Tip: If you wake up early enough you get two breakfasts._

\---

On the Monday of his second week at the Novak home, the inevitable finally happened. Dean was working on the piles of laundry that had backed up while Mrs. Novak had been out of town, when his cellphone rang. Since Bo was finally napping and he didn’t want the ringtone to wake the boy, he answered quickly without checking the caller id.

“Dean Winchester, I know you aren’t avoiding me.”

_Shit._ “Hi Mom.”

“ _Hi Mom_?” Mary mimicked. “You don’t call me for two weeks and that’s all you have to say for yourself?”

He closed the lid to the washer and got the machine running before moving back into the kitchen. “I’m sorry. I sent you a text that I was starting a new job and would be busy for a little while.”

She huffed into the phone and he knew the excuse was pointless. “I’ve been worried sick, Dean. You say you started some new job, but don’t tell me anything about it and refuse to answer my calls. Tell me the truth: is it porn?”

The fact that his mother had the same initial thought that he had was scary. “No, Mom. I’m working as a nanny for a family in West Hollywood. Room and board is included, plus a monthly stipend. It’s going great so far. They have the coolest son.”

“That’s my boy. Tell me about this family. Who are they? What do they do?” 

There were reasons behind him avoiding talking to his mother. Namely: getting asked twenty plus questions regarding work. “The dad’s name is Castiel Novak, his wife’s name is Gabby— but I haven’t met her yet. And the son is Boston, he’s three. The wife is pregnant with their second baby, but she’s only like four months along.”

“And their jobs?”

“He’s a writer and an editor, owns his own business. He said his wife works on a TV show, but that’s all I know. I had to sign a confidentiality agreement though—so who knows, maybe she’s famous.”

“Oh Dean,” Mary whispered. He could hear the worry seeping into her words. “I really hope you don’t get yourself in a bad situation. I don’t have the means to get you back home if something goes wrong.”

“I know, Mom.” Dean sighed, pulling out the ingredients he would need for Boston’s lunch when the boy woke up. “I think everything will work out, though. They seem like good people, the house is nice, and my room is huge. Castiel has been very clear on what he expects to be done and what isn’t my responsibility. So let’s at least give it a few more weeks before we start planning for the worst.”

\---

Over the next week, Dean decided that he wasn’t crazy and he really did enjoy living in the Novak home. Boston was a well behaved little boy and Dean hadn’t found it necessary to discipline him for anything yet. And Castiel? The older man was easy to get along with and had even offered to proofread a couple of Dean’s ENG 101 assignments.

Things were great. 

He had no idea that they could get better.

Standing in the kitchen making breakfast for himself one Saturday, he looked up at the sound of the front door opening. Castiel was home and had been sitting at the table eating cereal with Bo, when suddenly the boy jumped up out of his chair.

With an enthusiasm that Dean had yet to see, Bo ran towards the door. “Mommy! Mommy!”

Okay, Dean’s interest was definitely piqued now. He left his toast laying on a paper towel and turned towards the dining area. Whatever he had expected of Gabby Novak was definitely not what appeared before him. 

Bree McKenna, the star of NBC’s newest legal drama show, stepped into the room and smiled lovingly at Castiel. She looked exhausted, and definitely had a ‘baby bump’, but for the most part just seemed happy to be home as she leaned down to kiss her husband.

Since he hadn’t had the money for cable Dean couldn’t say that he knew anything about Bree’s show, but that didn’t mean he didn’t know who _she_ was. He had seen her face on more than a couple magazines, and had… _appreciated_ her spread in Maxim maybe just a little too much.

He felt his cheeks redden in embarrassment as he realized that he had seen his employer’s wife half naked. Not good. Not good.

Bree McKenna straightened and finally focused on him. She looked him up and down quickly, hands still resting on Castiel’s shoulders. “You must be Dean! Cas here told me all about how amazing you’ve been with Bo.”

“I uhh—” He had no idea what to say.

“Damn it, Cas.” She slapped her husband’s arm lightly. “You didn’t tell him who I was, did you?”

Castiel looked up from his breakfast, eyes flicking between the two of them as he tried to figure out what he had missed. “Sure I did. I had him sign the contract your agent made and then explained that my wife’s name was Gabby Novak. What else was I supposed to tell him?”

She rolled her eyes and moved across the room to stand before Dean. When she held out her hand to shake his, Dean stared at it in confusion. He was supposed to _touch_ her? And _not_ cream his pants?

“Hi Dean. I know this is probably overwhelming. I had hoped my—” she called a bit loudly over her shoulder, “— _ignorant husband_ , would let you know that I’m… somewhat well-known.. I see that he didn’t, but please… call me Gabby. I want you to feel comfortable around me.”

The amount of ugly grandmas that he had to picture in his mind while shaking Bree _fucking_ McKenna’s hand, was outrageous. But he managed. The early morning sunlight bounced off her straight auburn hair and sparkling green eyes. Her skin was so soft that he didn’t want to let go, but he also didn’t want to lose his job, so he dropped her hand and tucked his own into his pocket nervously.

“It’s uh… nice to meet you, Ma’am.” Sammy was never going to believe him when he told him who his new boss was. 

With a smile, Gabby reached out and tapped twice on his nose. “None of that. You’re family now, Dean, which means you call me Gabby or else.”

“Right.” He ducked his head with a shy grin. “Gabby.”

She watched him for another moment before turning back to the table. After a quick kiss to the tops of Boston and Castiel’s heads, she made an excuse about needing a shower and headed for the stairs.

Dean slowly turned back to the toast he’d forgotten about on the counter. Ice cold by now, in all likelihood. All he could think about was the fact that Bree McKenna would be sleeping in the room right next to his. _Shit._

\---

“You know it wasn’t very nice of you—springing me on the boy like that.”

Castiel looked up from the book he was reading and watched his wife as she unpacked her suitcase in the large closet. He was happy to have her home, especially considering how much morning sickness she had been dealing with. 

It was the fact that her stomach had been so upset lately that kept him on the bed instead of right up against her trying to initiate sex. After six years of marriage, Castiel knew that if Gabby wasn’t feeling good, she wouldn’t want to be touched. It was easier to let her come to him than chance getting his head bit off.

“Sorry, Honeybee. I’m so used to you just being, well… you. It’s hard to remember that I have to introduce Bree _and_ Gabby.”

Leaving her bag in the closet, Gabby stepped across the plush carpet to the side of the bed where Castiel sat. “You know,” she said, leaning forward over him, “your baby has been a little butt recently. I think I deserve something for all that I’ve had to deal with.”

“Oh?” He closed his book and set it on the table beside the bed, before stretching up to kiss her. “What do you deserve?” Castiel let his hands rest on her side, before dipping beneath the shirt that his wife wore. “My touch? My tongue? My cock?”

Gabby grinned, desire in her eyes. “I’ll take all of the above.”

\---

When Dean realized that his bedroom was right next to where Bree McKenna’s bedroom was, yeah, it sent a shiver down his spine. Imagining the television star laying in bed in a lacy ensemble, was enough to have his cock half hard for most of the day.

It was truly awesome being that close… _in theory_.

But as he laid in his bed and suddenly heard the cries of ecstasy coming through the walls, Dean knew that he was in trouble. He also understood why his empty bedroom had been between the master suite and Boston’s room.

Gabby was a screamer.

_“Fuck yes, Cas! Mmm… yeah, fuck me with your tongue!”_

Considering that he was listening to his employers having sex, Dean really shouldn’t have been so turned on. But after tossing and turning for ten minutes, he heard the soft knocking of the bed next door hitting the wall and remembered that damn Maxim article.

“Fuck,” he whispered. Shoving the covers back, he pushed his boxers out of the way and wrapped his hand around his hard cock. 

As he accepted the fact that he was probably going to hell, and would never be able to look Gabby Novak in the eye again, he jerked off to the sounds of her moaning. God, he hoped that the Novaks weren’t the type to have sex constantly—otherwise, he was going to die of embarrassment and blue balls.


	3. Chapter 3

**Notes for the Chapter:**

> I'd like to say the somewhat daily updates will continue, but I can't promise that. So enjoy it while it lasts. ;)

_Toddler Tip: Roses are red. Violets are blue. I broke the DVD player._

\---

It took a month for Dean to feel well and truly settled in the Novak home. It wasn’t the most glorious job when you factored in the cleaning, cooking, and endless loads of laundry, but seeing his first monthly check in his hand made it worth it. Not to mention the fact that Boston really was a cool kid. He was shy and reserved, but surprisingly smart. And the only time he really gave Dean a headache was around mealtimes. Castiel had explained that because of Bo’s small size, and the fact that he was on the lower end of a ‘healthy weight scale’, it was important to make sure Boston ate as much as possible.

Dean had figured out pretty quickly that Bo didn’t exactly hate food—he just had more important things to worry about than sitting down to eat. A lot of times Dean found that making a game out of mealtime made it pass without a struggle (omelettes or sandwiches that looked like smiley faces were always a good go-to), but other times even that didn’t work.

But considering that was the only downfall of watching Boston, Dean decided he could live with it.

What he was struggling more so to live with was the … _intense_... atmosphere that surrounded Castiel and Gabby when they were in the same room. Even after so many years of marriage, the two obviously hadn’t lost the spark in their relationship. 

It had Dean so sexually frustrated that he was already preparing to go out on his next night off and get laid. Unfortunately, that was a whole week away.

On Monday evening it seemed to take forever to get Boston down for the night. Dean was in the process of putting away the laundry from that morning and carried Castiel and Gabby’s basket upstairs. He hadn’t seen the couple in over an hour, but their door was still open at the end of the hallway, and he could hear the TV still on.

Laundry basket in hand, he walked to the edge of their bedroom and stopped. His body was frozen as he stared into the room. Directly across from the doorway was a six foot tall mirror, placed strategically as part of the decor. Though he couldn’t see the bed from where he stood, Dean could definitely see the reflection of it.

Castiel sat on the edge of the bed, shirt shoved up along his chest and boxer-briefs around his ankles. On the floor in front of him Gabby knelt in a black, skin-tight top and a black thong. 

Dean watched in fascination, feeling his cock harden and his mouth go dry as Gabby’s head ducked forward, moving up and down rhythmically.

_Fuck._ Dean realized instantly that he was watching Bree McKenna give a blowjob, and… he had never seen anything hotter in his life.

He knew it was pervy and that he should just drop the basket and walk away, but he _couldn’t_. The sight of Castiel grabbing a handful of auburn hair and using it to guide his wife’s movements was something that Dean had never expected to see. Hearing the couple have sex through a wall was one thing; seeing it live in person was completely different. 

It was better.

Shifting the basket quietly, he reached his right hand down to press against his cock, trying to ease some of the pressure.

Dean’s attention was so focused on watching Gabby’s movements, that he didn’t even notice bright blue eyes staring at him in the mirror. 

“Mmm, Gabby,” Castiel moaned. He pulled her head back until his cock popped free from her plump pink lips and an obscene string of drool ran from her mouth back to his dick. “Fuck, you’re hot. You going to suck me dry, Honeybee? Just like you promised?”

“Please,” she begged. Her tongue slipped past her lips to run along the tip of his cock. “Come in my mouth.”

God that was hot. Dean watched Castiel shove his cock back in his wife’s mouth and found himself wondering just how much she could take. He wanted so badly to find out. He heard Castiel gasping in pleasure and looked up to the other man’s face.

When Dean’s eyes met Castiel’s, he felt his blood run cold. _Fuck._ Yeah, he was definitely out of work now…

Except—instead of looking angry, Castiel winked.

A second later, the man was coming with a soft shout, hips jerking off the bed as he held his wife in place. She kept her mouth locked around his cock, not spilling a drop of his seed.

When Castiel was finally done coming, Gabby pulled back and moaned as she made a show of swallowing everything she had collected in her mouth.

It was at that moment, that Dean shuddered and felt his own orgasm hit him, his dick coming untouched in his pants. _Oh God._ He dropped the laundry basket to the floor and hurried to his own room. 

Despite the fact that he had just came, when he stripped from his sticky clothes and climbed into the shower of the ensuite bathroom, Dean couldn’t help jerking off _again_.

\---

On Tuesday morning, Dean still half-expected to get fired—even after _the wink_. But when he woke up at six and walked downstairs to get a cup of coffee before the rugrat woke up, everything seemed surprisingly normal. Gabby always left for work early, so she was halfway out the door and did nothing more than wave goodbye at Dean before the door shut behind her.

Castiel stood in the kitchen, dressed in a suit and fixing a bagel for breakfast. When he looked over and spotted Dean, he smiled briefly before going back to what he was doing. “Good morning, Dean. I trust you slept well?”

“I did,” he answered softly. He scratched a nervous hand along the back of his neck, wondering if he should say something in regards to the previous night. How exactly did one broach the subject of _So your wife gives good blowjobs, eh?_ He decided quickly that he wouldn’t mention it unless Castiel did. Grabbing a cup, he moved to the coffeepot beside where Castiel stood, and motioned to the man’s suit. “You’re a little more dressed up than normal. Big meeting?”

“Very big. I’m in talks to get one of my television scripts picked up by a network. Today is the final negotiation.” Castiel frowned, his bagel held halfway between his mouth and the counter as he watched Dean for a moment. “You know, we never discussed this when you first started, but our family has a lot of traveling happening soon. Are you going to be okay with that?”

Dean’s stomach dropped as he imagined the worst. ‘We’ll be gone for three months, Dean, and won’t need your services at that time.’ _Fuck._ “I, uhh…”

“I think the first trip is to Manhattan, in two weeks. Gabby has a condo there by Central Park. I’m sure Bo will love having you around to walk him through the park. He’s a big fan of the zoo and will probably try to drag you there every day.”

It dawned on him suddenly that Castiel wasn’t talking about leaving Dean in Los Angeles… he was talking about taking Dean with them wherever they had to travel. Despite his damned fear of flying, Dean grinned at the prospect of seeing a place like New York City. “I’d love that. I never did get to see much outside of Kansas.”

Castiel reached out, laying his free hand on Dean’s shoulder casually. “Don’t tell Gabby that. She loves to travel and will have us flying all over the world just so she can show you new things.” The touch lingered for another few seconds, before Castiel finally pulled away with another grin. “I have to get going. I’ll see you and Bo for dinner.”

Dean barely had time to say ‘Bye’ before Castiel was carrying his breakfast and a travel mug of coffee out the door. 

A few minutes later, when Dean was refilling his own cup with coffee, two small feet pitter-pattered into the kitchen. He turned to look at Boston, standing on the edge of the kitchen floor and looking half asleep with his blonde hair sticking up and a teddy bear in one hand. 

“Good morning, sleepy head. Cheerios or eggs?”

Boston yawned, scratching at his wild hair and contemplating the question. “Cheerios,” he finally answered. While Dean got his cereal, Bo moved to the table and positioned his teddy bear haphazardly in one seat, before climbing into the one next to it. “Dean?”

“Yeah, kid?”

“Can we go on a bike ride today?”

Dean carried the bowl of cereal over to the table and placed it in front of the boy before smiling at him. “I’ll make you a deal. If you eat all of your cereal, and then all of your lunch, we will go on a bike ride this afternoon.”

Ever the tough negotiator, Bo contemplated the deal for a few long seconds, before nodding. “Okay!”

“Sounds like a plan then, kid.” Dean ruffled the boy’s already messy hair, before sitting down across from him with his cup of coffee. “Your dad said we’re going to New York in a couple weeks. He says you’re a big fan of the zoo…”

At even the mention of the place, Boston lit up. For the next half hour, Dean listened intently as Bo explained about the various animals and which were his favorite and why. 

The kid was just way too smart for his own good.


	4. Chapter 4

_Toddler Tip: Bag of sugar opened by itself. Making snow angels._

\---

If there was anything harder than traveling with a three-year-old, it was traveling with a celebrity _and_ a three-year-old. Dean was more than a little overwhelmed by the crowds of people and security guards and paparazzi and _flying_. It was just too much.

Thankfully, his job was clear: keep Boston beside him and happy. Dean kept his head down and the boy’s hand tucked into his own as he followed Castiel and Gabby through the airport. They were both far less wigged out about everything going on around them—showing their experience with the whole mess by walking calmly and focusing on where they were headed. 

After a crazy and stressful trip through airport security, Boston finally reached his breaking point. It was after one in the afternoon and the boy was two hours past his normal nap time, which meant that Dean wasn’t surprised at all when Bo flopped down on the airport floor with tears in his eyes. A few steps ahead, Gabby and Castiel both turned back to see what the problem was but since they were loaded down with carry-on bags, they couldn’t exactly help. 

“I got it,” Dean said, waving at them. He knelt down next to Bo and brushed the boy’s hair from his face. “Hey kid, what’s wrong? Tired?” Tears running down his cheeks, Boston nodded. “Alright, how about I carry you until we get on the plane? Does that work?”

They had, of course, brought a stroller. But Boston had stood at the ticket counter and made an adamant argument that he was old enough to walk and didn’t need a stroller—so they’d checked it with the rest of the luggage.

Instead of replying, Bo simply raised his arms so that Dean got the message that he did, indeed, want to be held. After picking the boy up, he smiled when Bo rested his head on Dean’s shoulder. The kid was obviously exhausted and seemed to be about as annoyed with the airport crowd as Dean was. 

Hurrying forward, he joined Gabby and Castiel and followed them towards the proper gate. 

With the minor toddler breakdown, Dean had forgotten all about the fact that they were about to get on an airplane for a six hour flight. Until, of course, the gate agent called for first class to begin boarding. Biting back his nerves, he held Boston a little tighter in his arms as he followed Castiel and Gabby and handed over his boarding pass to be scanned. Stepping onto the plane made everything seem more real, and his heart started racing as he stood at the front of the aisle and stared down the length of the fuselage. Yeah, he was definitely going to have a panic attack. 

“Dean?”

Shaking the thoughts from his head, he looked to Gabby who was watching him with knowing eyes. “Yeah?”

She motioned to the right side of the plane, where Castiel was getting settled. “Why don’t you let Bo sit with Cas? You and I can get to know each other a bit.” 

Since it was first class, there were only two seats to a row, in comparison to the regular cabin which held three seats close together. Suddenly, Dean didn’t know what was more nerve-wracking: the thought of flying or the thought of sitting beside Bree McKenna the whole time. “Are you sure? I can watch him.”

“It’s fine. They’ll both be asleep as soon as we take off—I know how my boys are.” She pulled Bo from his arms and handed him to Castiel, who got the boy settled into the seat by the window. When Gabby looked back at Dean, she smiled. “Aisle or window?”

 _Can I just crawl underneath the seat and die, instead?_ “Uhh… window.”

She stepped aside so that he could get past her and into her seat, and he tried to hide his shaking hands as he quickly buckled the seatbelt and relaxed into the leather. 

Gabby dropped gracefully into the seat beside him and pushed a large tote bag behind her feet. “I always bring lots of snacks and activities for when Bo gets bored on the plane. So if you get hungry or want to play with the iPad, let me know.”

“Thanks,” he whispered, shifting a bit uncomfortably in his seat. Through the window he could see the airport personnel loading luggage onto the plane. Watching such a mundane task take place was hypnotic and he started to relax a little—until the guys finished and drove off.

The pilot’s voice came over the speaker, letting the passengers know that they were going to begin taxiing down the runway and would be taking off at the scheduled time. _Shit._ Dean felt the panic boiling up in his stomach again and prayed that he didn’t make a fool of himself by puking in front of Bree McKenna.

“Dean.” Gabby drew his attention to her, as she laid her hand on top of where his was clinging to the armrest. “I know you’re freaking out right now, but just take a deep breath and stay calm, okay? I promise you that everything will be alright. I fly all the time, and once you let go of the fear, I assure you that you’ll enjoy it.”

He doubted every word she said, but her touch was soft on his hand so he forced himself to breathe the way that she was demonstrating. 

It worked just fine… until a runway cleared and suddenly the plane was turning and beginning to speed up.

“Oh God,” he mumbled under his breath.

The plane jerked, gaining even more speed as it rushed towards the end of the runway. Dean slammed his head back against his seat, squeezing his eyes shut and praying to whatever God would listen. At the same time, his hand flipped over and his fingers tangled with Gabby’s as he clutched desperately at her.

While the plane continued to steadily rise, he began softly singing under his breath, using the last technique that he knew of to calm himself down.

Gabby leaned closer, her hand still holding on tight to his. “Dean?” she whispered. “Are you singing Metallica?”

“Helps me relax,” he answered. After a moment, Dean realized that she had heard his soft mumbles and immediately recognized the tune. His eyes shot open and he stared at her. “You like Metallica?”

Her face lit up with a grin and Dean contemplated just how beautiful she was. Of course, her next words made her even more awesome. “Lars is a family friend. I had them agree to do a special concert a couple years ago when Cas turned thirty. It was amazing.”

Dean was pretty sure his jaw hit the dirty airplane floor at that point. “Marry me,” he stated.

Gabby reached up with her free hand to bop him gently on the nose with her finger. “Cute.”

\---

About an hour into the flight, Dean had calmed down enough to be bored. Just as Gabby had predicted, across the aisle both Castiel and Boston were snuggled up and asleep. Gabby was flipping through the pages of a script, but seemed to be just as bored as Dean was.

“Did you move to LA to be an actor?” Gabby asked, noticing his attention was on her script. She flipped a page as Dean shook his head. “No? Then why?”

“If you’ve ever been to Kansas, then you know the answer to that. The place sucks. I wanted to leave last year when I hit eighteen, but my little brother was struggling with fitting in at school and my mom begged me to wait another year. So I stuck it out, and waited a year, saved every dollar I could, and then I left.”

“I can kind of understand. I grew up in a small town in Texas and couldn’t wait to get out. Difference being, I knew I wanted to be an actress.” She closed her script and put it back in her bag, before pulling out a bag of kale chips and offering Dean one. “Cas says you aren’t sure what you’re going to study, either. I like that, Dean. I like that you’re just taking life as it comes to you, trying to figure out what you like best.”

Dean pulled out a piece of kale and stared at it skeptically. He had fed Boston more than a few of the things, but that didn’t mean he had ever had the nerve to try one. 

Gabby leaned closer, lowering her voice. “Try it. I promise it won’t kill you.” He took a bite and immediately made a face, causing her to laugh. “Sorry. Forgot to mention that my pregnancy cravings make all kinds of weird shit taste good. I may have dumped curry powder in this bag.”

He quickly grabbed for the cup of water sitting on the tray in front of him, and tried to get the overwhelming flavor out of his mouth. “Oh my God, you lied, Gabby. I think it _is_ going to kill me.”

Gabby took the piece of kale from him and popped in her mouth, before reaching up to press the call button for the flight attendant. When a woman walked up, Gabby motioned beside of her. “Can you bring him a Coke, please? He’s suffering from overwhelming curry ingestion.” 

The woman quickly brought him the drink and Dean took it gratefully. 

“I think,” Gabby said, her voice low, “that the flight attendants might be sleeping together.” 

Her eyes were focused on the front of the plane. Shifting over closer to Gabby, Dean tried to see what she was looking at. “Did she just grope him?”

“She totally did. Think they’ve done it on the plane?”

Dean frowned. “That’s not actually possible right? That bathroom is tiny!”

“Oh Dean.” Gabby smirked at him. “Anything is possible if you’re horny enough.”


	5. Chapter 5

**Notes for the Chapter:**

> I love how everyone is trying to figure this story out. Please keep in mind that this is only chapter 5 and I don't intend to rush this story at all. But to appease your need for answers, have this:

_Toddler Tip: We’re going to Target for paper towels. See you in three hundred dollars._

\---

New York was something like he’d never seen before. Los Angeles was big, no doubt, but New York City was all of Los Angeles rolled into one small island. The buildings, the people, the cars… it was a lot to take in.

After they landed in LaGuardia, an SUV was waiting outside to pick them up. Dean climbed into the third row, beside Boston, while Castiel and Gabby sat in the middle row behind a new pair of bodyguards. Since Bo was happily engrossed in a book, Dean watched through the window at the passing buildings, all lighting up the black sky. 

They drove a few miles before Castiel turned, glancing over the seat and smiling at Dean. Feeling the gaze, Dean looked to the older man, feeling his heart race at the sight of that smile. It lit up blue eyes brighter than the city lights. 

“What do you think, Dean?” It wasn’t just a question; Dean could see that Castiel was genuinely interested in Dean’s thoughts about New York.

“It’s—a lot to take in. Makes Kansas City look like nothing.” He hesitated, before finding the courage to ask, “Do you think we could go see the Statue of Liberty at some point? I could send a picture to my mom and Sammy—God, they’ll be jealous.”

Castiel nodded. His arm was resting on the length of the seat back, his fingers tickling gently through Gabby’s auburn hair as she messed with her phone. “I think Gabby has a camera you can borrow, if you want. I don’t have any meetings scheduled tomorrow, so why don’t we make it a tourist trap day? Give you time to get acquainted with the city a bit.”

Proving that she was listening in on the conversation, Gabby spoke up. “Way to make me jealous. Wish I could hang out and do fun stuff instead of photo shoots.”

Dean laughed, his eyes going back to the window just in time to see the Empire State Building coming into view. “I’d like that, Cas.”

Castiel’s eyebrows shot up, and Gabby looked up from her phone and over to her husband in shock. “Did he actually just—”

“Wow, Gabby, I think the boy has finally figured out that he can relax around us.”

Dean’s eyes shot back to them in worry. He realized belatedly that he had indeed said Cas instead of Castiel. Instead of anger, though, Gabby and Castiel just looked amused. He pouted, eyes focusing back outside. “You two are mean.”

\---

Gabby’s condo actually seemed to be larger than their home back in L.A. It was open and airy, with sleek modern furnishings and large expensive looking paintings on the wall. Dean’s room was comfortable and _thankfully_ not right beside Castiel and Gabby’s room. He managed to sleep through the first night with only one wet dream.

The next morning, since their systems were still adjusting to the time change, they didn’t leave for their big tourist adventure until almost noon. Thankfully, Bo seemed well rested and ready for a day spent hanging out with his father and Dean. He even, after a car ride to the ferry station, was more than happy to sit in his stroller instead of demanding to walk.

They went through security points that seemed more intense than airport security had been, before finally boarding the ferry with their passes securely tucked in the backpack on Castiel’s back. Dean steered the stroller through the maze of people towards one of the open decks where they could watch the trip progress. He had to admit, if only to himself, that he had never been so excited about being a tourist.

Castiel slid up next to Dean, body pressed a little closer than necessary, arm brushing against Dean’s. He didn’t seem to notice or care that he was well inside of Dean’s ‘personal bubble’—but Dean noticed immediately.

He swallowed past a lump in his throat and gripped the stroller’s handle just a little tighter.

The ride to Liberty Island was—thankfully—quite short. Unfortunately, Castiel never moved away, putting Dean’s nerves on a jittery race through his body and making it impossible for him to focus on the amazing view of the city.

They disembarked the ferry with the flood of other tourists and Boston immediately began questioning his dad about the statue. Dean listened in, but remained quiet. It was interesting to see father and son bonding over their shared interests, but it immediately made Dean’s heart ache with the reminder that he never got the same opportunity with his own father. 

He looked away, focusing on the statue and the cityscape in order to bite back his emotions. 

“Dean?”

Startled from his thoughts, he looked up to see Castiel watching him intently. “Yeah?”

Castiel held up the digital camera that he had brought with them. “Should we ask someone to take our picture?”

He nodded and watched as Castiel soon flagged someone down to do the honors. When he walked back over, he smiled softly to Dean before reaching down to unbuckle Bo. 

With the boy held in his arms, he moved right next to Dean. Dean shifted, not quite sure how to stand, but Castiel made the decision for him. He pressed close against Dean’s side again, with Bo tucked securely between them and smiling like a goofball. 

“Say cheetos,” the little boy called out.

Dean and Castiel laughed, and it was easy to hear a few people around them also chuckling. A few camera clicks later and Castiel pulled away, setting Bo in his stroller and telling him to buckle up, before thanking the fellow tourist and taking the camera back. 

“Come on,” he motioned. “We have a tour and a trip up to the crown to take.”

With a nod, Dean made sure Bo was settled before pushing the boy after his father.

\---

A few hours later, they had all pleasantly reached their ‘tourist’ limit. Instead of calling the car to pick them up, or taking a taxi home, Castiel was adamant that Dean needed to experience the New York subway system.

Considering the terrible smell of decay and urine, he wasn’t entirely certain why the older man had reached that conclusion. But even still, he was tired of walking and since they had quite a few stops to go, he happily sat down beside Castiel on the train. 

The stroller sat in front of him, wheels clenched between his feet so that it didn’t roll around when the train slowed or accelerated. Boston had passed out right as they were exiting the ferry station, and was currently slumped against the side of his stroller at an angle that had to hurt. 

“Did you have fun?” Castiel asked, leaning closer so that Dean could hear him over the sound of the train.

“I did. Thanks for taking me. Like I said, my little brother is going to be super jealous.” Dean pulled his gaze from those piercing blue eyes and stared down at the wheels of the stroller and his own worn out tennis shoes. He missed his brother. One day, he promised himself, he would bring Sammy to see New York.

A loud announcement overhead let the passengers know which station they were approaching, and the train cars jerked as they slowed to a stop. The motion caught Dean off-guard and he slid and bumped into Castiel’s side. When he looked up to apologize, the words were cut off by the sight of a smile on the man’s face. 

He quickly pulled his eyes away again. This time, he glanced around at the people on the train, taking note of the passengers coming and going and the ones settled in for an extended journey. 

Across from them, an old Hispanic woman caught his attention. She was dressed in a maid’s uniform and clutching a large handbag to her chest… and watching them. The women didn’t look nervous or angry though; she looked happy, laugh lines crinkling around her lips and eyes as she smiled. 

The train started moving again and she noticed that she had caught Dean’s attention. She motioned to them and spoke, accented voice carrying across the train. “Your family is beautiful. My son… he and his husband just got approved to adopt. Seeing you and your family, it gives me hope for their happiness.”

Dean opened his mouth, ready to tell the woman that she had assumed wrong. That Boston wasn’t his and Castiel… also wasn’t his. 

Before he could reactspeak though, Castiel’s hand landed on Dean’s knee and the older man spoke for him. “Thank you. Tell your son that we wish him the best of luck. Children are a lot of work, but they are worth every minute.” He turned, meeting Dean’s confused look. “Right, Dean?”

The confusion skyrocketed. Instead of feeling like Castiel was teasing him, he could see that the man was sincere in his words and intentions. Which, quite honestly, fucked with Dean’s head. He managed to choke out a soft, “Uh… yeah,” but doubted the woman could actually hear it across the train. He didn’t check if the answer was enough, though, because he was stuck still staring at Castiel.

Like the night that Dean walked in on Gabby and Castiel, Castiel winked at Dean, before looking away with the station announcement played overhead. 

“This is our stop.” He stood and Dean shook his head before quickly following suit. 

Unfortunately, it was Dean’s first time on a subway train, and he had stood up before the train stopped at the station, completely forgetting about the consistent stop-jerk motion. He stumbledslipped, balance completely gone and feet still tangled around the stroller.

His body hit a hard surface and he was quickly stabilized, but instead of hitting the floor, like he expected, he landed against Castiel’s chest. Castiel reached up immediately, arms wrapping around Dean to steady him. 

“Shit,” Dean gasped, heart racing. He looked up, thankful he hadn’t fallen and immediately surprised by how close his face was to Castiel’s. _Oh._ Why was the other man still holding him? He was clearly standing on his own two feet again!

Castiel leaned closer, and Dean’s eyes tracked down to his lips on instinct. Were they going to kiss? Why would Castiel kiss him? Was he still playing up the ‘fake’ relationship that the old woman had assumed? Didn’t Castiel realize that Dean was one hundred percent, certifiably, got the membership card to prove it, _straight_?

The train doors clicked and slid open, and Castiel easily pulled away, completely unphased. He told the woman to have a good day, and motioned for Dean to push the stroller off of the train. 

They were back up on the busy New York sidewalk, before Dean’s head stopped spinning. Though he wanted to just brush the whole thing off and ignore it like the blowjob incident, he knew that he couldn’t. It would eat away at him and drive him completely insane. 

There were three blocks before they’d reach the condo building—plenty of time for an explanation. “Cas, why did you lie to that woman?”

Castiel stopped, waiting at a crosswalk for the light to change. He glanced at Dean briefly, before focusing ahead once more. “Did you see how happy she was? What was the harm in letting her experience that small moment of joy?”

What was the— _what was the harm?_ Dean stared at Castiel like he was insane. “But you can’t just—” He stopped, trying to figure out why he was so upset. Was it the fact that Castiel had let the woman believe they were a couple, even though he was married? Or the fact that he let her believe Dean was gay? Something occurred to him, and he looked back to the man. “You know I’m straight, right? I mean, I know not many guys would take a job as a nanny, but that doesn’t mean I’m into dicks.”

The light changed then, and Castiel started walking across, leaving Dean to push the stroller after him. When they were back on the sidewalk, Castiel spoke. “Is that a Kansas thing?” He looked over to see the confusion in Dean’s eyes, before elaborating. “The fear of someone assuming you’re gay.”

Dean glared. “I’m not—”

“I know. You’re not gay.” Castiel shook his head. They continued for the rest of the walk in silence. When they stepped inside the first set of doors of the condo building, Castiel stopped and reached out to grab Dean’s elbow so that he stopped as well. They were in the small atrium, cocooned between two sets of doors that would keep anyone else from hearing what was spoken. Castiel waited until Dean’s attention was completely on him, before speaking. “For the record, Dean, I’m not gay either.” He leaned closer until the space between them had all but vanished. “But that doesn’t mean I’m not man enough to admit that when I came that night—that night that you were spying on Gabby and I—I almost moaned your name. Seeing how turned on you were? Sent me over the edge far faster than it should have.” 

Dean’s heart raced and he couldn’t remember how to breath, as Castiel’s face leaned towards his. He was staring at those lips again, despite himself.

Those lips opened and a deep voice escaped, sending a chill down his spine and making his dick twitch. “Maybe,” Castiel whispered, “you should consider trying new things.”


	6. Chapter 6

**Notes for the Chapter:**

> Top!Cas/OMC/OFC in this chapter.

_Toddler Tip: The only things that you should ever willingly share are viruses._

\---

“I didn’t know we were going to see him this trip.”

“Well I had no intention of it playing out like this, Cas, but it’s not like I can keep it a secret when I get to town. He’s in the business— _he knows_.”

“What about Dean?”

“We tell Dean that we have to go to a fancy dinner party or something. This is why we have a nanny.”

“Gabby… you and I both know that Paul is going to cause drama. Why else would he contact us after so many months? I’ll go along with this, but I’m telling you, if he steps out of line even slightly—we are _leaving_.”

“Fine. Whatever. He promised he would behave.”

“Yeah, like he hasn’t made that promise before.”

\---

If Mary Winchester knew how often her eldest son managed to eavesdrop on his employers, she would skin his hide.

It wasn’t Dean’s fault, though. He couldn’t help the fact that he was on his way to tell Gabby and Castiel about Boston’s cold when he overheard their loud conversation in the bedroom. The couple didn’t seem at all worried about the fact that a closed bedroom door didn’t keep their privacy well… private.

Deciding that he could tell them about Bo when they came back out of the room, he turned back around and moved down the stairs to the living room. _Despicable Me_ was playing on the large flat screen TV, and Boston sat on the couch wrapped up in two different blankets and clutching a stuffed dinosaur. 

“Do you want me to make you some soup, Bo? I bet I can remember the recipe for my mom’s ‘get better soon’ soup.”

Sniffling, Bo looked up at him. He looked pitiful, and it had came on quickly after he woke up from his nap. “Can I have a space cheese?”

Anyone else would probably be confused by the request, but Dean knew immediately that Boston wanted a grilled cheese sandwich cut in the shape of a flying saucer. “Sure thing, kid. Holler if you need me.”

As he walked to the kitchen, he mused over the fact that it had only been seven weeks and he already knew Boston well enough that he could speak the kid’s language. Then again, the kid reminded him more and more of Sammy with each passing day. 

Thinking about his brother tugged at his heart. He had been meaning to call Sam, but everytime he thought about it, the time difference didn’t work out in his favor. Pulling out his phone, Dean took the time to punch in a reminder alarm so that he could call and talk to both his mom and his brother that evening. Once the phone was tucked back in his pocket, he focused on making lunch for Bo, just the way he liked it.

Unfortunately, the mundane task of standing over a stove and cooking a grilled cheese made his thoughts drift.

He could still hear Gabby and Castiel’s earlier conversation playing out in his head, and he couldn’t help the questions that appeared as a result. Mainly: who was _Paul?_ Why was Castiel so worried about meeting the man?

And why had Castiel said _‘What about Dean?’_ like Dean’s reaction to them going out with a friend would matter?

Which lead to a whole new set of thoughts involving the day before in the building lobby.

_No._ He would _not_ think about that moment _again_. He had already tossed it around so many times in his head that it had turned into a warped version where Castiel slammed him against the wall and kissed the air out of his lungs. Dean would not give in to the need to analyze Castiel’s words.

“Dean.”

He jumped, knocking into the pan and sliding it back off the burner. _Shit._ Hearing the subject of his thoughts speak from the edge of the kitchen was not what he expected. He righted the pan and flipped the sandwich one last time, but didn’t dare to look at Castiel.

“Yeah?” He slid the sandwich onto the plate he had already set out, and quickly shut off the stove.

“Is it alright with you if Gabby and I go out to meet a friend for dinner this evening?”

“Yeah, of course.” Dean continued to keep his back to Castiel, hoping the man would take the answer given and leave the kitchen. Not that his presence flustered Dean or anything…

A firm body suddenly pressed up against Dean’s back, and _holyshitwhatthefuck_. Castiel held Dean in place with two hands on his biceps, and leaned his head forward to look over Dean’s shoulder.

What was breathing, again? 

“What is that?” Castiel asked, his breath tickling along Dean’s ear. 

Dean frowned, his heart racing and his body stiff as he tried to figure out what exactly Castiel was talking about. Considering he was on the wrong side of Dean’s body to feel the beginnings of Dean’s erection—

_Oh. The sandwich. Right._ “It’s space cheese.”

Castiel’s right hand tickled down Dean’s arm. “Space cheese?”

“Grilled cheese shaped like a spaceship. I’ve found that making the food into fun shapes gets Boston more interested in eating it.”

Dean felt Castiel gasp softly at the words. “You’re amazing, Dean,” he whispered. Castiel pulled away, and Dean could have sworn that he felt the ghost of a kiss on his hairline, but when he turned around… Castiel was already gone.

\---

12:37 a.m.

Dean stared at the clock like it was stupid and suddenly lying to him. He had only been in bed for a little over an hour, just long enough for the edges of a deep sleep to start pulling at him. Something had woken him up, though, and it took his brain a few minutes to catch up before he realized that he had heard a crash from downstairs. 

Immediately worried that Boston had woken up and needed something—or worse, that someone had broken in—he climbed out of bed and flicked the lamp on. With the soft light he was able to find his sweatpants and pull them on over his boxers. 

He quietly stepped out of his room, barefeet padding across the carpet. Across the hall, Bo’s doorway was still cracked open like Dean had left it earlier when the boy fell asleep. He stepped forward anyways, pushing it open far enough to check that Boston was still in bed. He was, thankfully, but that didn’t explain the noise downstairs.

Suddenly there was another loud bang, followed by an equally loud ‘shhhh’ and giggling. Drunk giggles, by the sound of it. 

Dean hoped that it was Gabby and Castiel and not the noisiest, drunkest burglars known to man. He walked downstairs, still remaining as quiet as a mouse, and peered into the living room.

The room was empty, but more giggling sounded from the direction of the kitchen and dining area. Dean was two steps down the hallway, when he heard a voice.

“God damn it, woman, stop giggling.” 

_Castiel._ Well, that was a relief. 

Considering all the things that Dean had stumbled upon since he started working for the Novaks, he _knew_ that he should just turn around and walk right back upstairs. Whatever Gabby and Castiel were up to was absolutely none of his business and he should just go back to bed. 

All of that made sense in his mind, but it didn’t keep his feet from moving him closer to the edge of the hallway. All he had to do was peek around one little corner and his curiosity would be settled. 

As he got to the edge of the wall, he heard moaning. The crazy thing was, though, that it didn’t sound like Castiel _or_ Gabby. 

Holding his breath, he leaned forward and looked into the open space of the dining room.

He should have gone back to bed. 

On the large oak table, Gabby was laid out on her back. Her shirt was gone and the lace of her bra cups were pulled down to expose her breasts, which she happily clutched. The short leather skirt that she had worn when she left the house earlier that night, was shoved up around her waist. 

Dean couldn’t see her pussy though. No, that was hidden by an unknown man’s head, as he obviously worked hard to please her. Behind the stranger, who was completely naked and leaning over the table’s edge, stood Castiel. 

Pants and underwear around his ankles, Castiel’s hips were moving at a steady pace as he fucked the man who was eating out his wife. His hands were gripping the other man’s ass hard enough to leave marks and his groans made it obvious that he was _really_ enjoying himself.

_Holy. Shit._ Dean tried to pull his jaw up from the floor but he couldn’t. He was shocked; frozen where he stood as he watched the lewd acting taking place on the table. 

“Fuck, Paul, so good,” Gabby gasped, her fingers tangling into the man’s hair.

Well… that explained who _Paul_ was.

As Dean watched, Castiel bent forward over Paul and kissed along the back of his neck. Like a freight train, the memory of earlier in the day when those lips had skated across his own skin slammed into Dean. He stumbled, knocking hard enough into the wall to make a picture rattle. Freezing once more, he expected someone to notice his presence—but the three were too busy and too drunk to hear.

He turned in a rush, feet taking him quickly back upstairs without any care of whether or not they heard him. Odds were that they obviously wouldn’t. 

When he shut his bedroom door softly behind him, he leaned back against it and tried to control his own thoughts. He couldn’t figure out what was going on—why the scene had bothered him so much.

It was only after laying down in bed and staring up at the ceiling for a solid twenty minutes, that it dawned on him.

He was _jealous._


	7. Chapter 7

_Toddler Tip: I get that vegetables make you stronger but so will any kind of adversity._

\---

Castiel was frustrated. It was a beautiful Sunday afternoon and he wanted to take his son to the zoo, but the boy was having none of it.

“Why not, Bo? You love the zoo. We can go see the hippos—” Arguing with Boston was like arguing in front of the supreme court. But then again, maybe all three-year-olds were like that. 

Standing in the middle of the living room, Bo crossed his arms over his chest and glared at his father. “No. We have to make space cheese for Dean. So he feels better.”

“Dean?” His eyes drifted to the staircase automatically. He hadn’t seen their nanny in two days, since they had decided that Dean could have the weekend off to enjoy himself in New York. If Dean had left the condo at all since Friday night, he had done it without anyone else’s knowledge. Dean’s absence didn’t explain Boston’s worry though. “Bo, why do you think Dean is sick?”

“He has my cold!”

Well that was news. He tried to remember the last time he had seen Dean, and whether or not the younger man had seemed sick. Wednesday night was the dinner with _Paul_ and subsequent afterparty that Castiel could barely remember. Thursday he had meetings all day with network executives and didn’t make it home until well after eleven that night. And Friday evening they met up with Paul again for a trip to a local club. 

Which meant, other than brief hellos in passing, Castiel hadn’t actually spoken to Dean since Wednesday afternoon when Dean was cooking Boston lunch. 

How long had Dean been sick? He knelt down in front of his son, “Bo, how do you know Dean is sick?”

Bo rolled his eyes at his father’s question—like he couldn’t be bothered to deal with such ignorance. “I went in his room. Can we make him space cheese?”

A light grip on Boston’s shoulders, he steered the boy towards the couch. “Hang out here and watch cartoons. I’m going to check on Dean, see if he wants anything to go with his space cheese, and then you can help me in the kitchen.”

Boston seemed apprehensive and ready to argue, but finally settled onto the sofa when Castiel gave him a reassuring smile. After, Castiel turned and quickly made his way up the stairs to Dean’s bedroom. He paused at the door, hand already resting on the doorknob and ready to turn it and go in. He should probably knock, but he was worried Dean would deny him entrance.

Meeting somewhere in the middle, he placed two soft knocks on the door as he pushed it open. Whatever he was expecting to find inside of the bedroom, was definitely nowhere close to what he actually saw. 

The curtains were drawn, leaving the room dark and stuffy, and Dean was little more than a lump on the bed. He was bundled in blankets pulled up to his chin, but still seemed to be shivering. Next to the bed on the small nightstand was a clump of used kleenex and a half empty box of the tissues. 

Castiel stepped forward, flicking on the lamp beside the bed and looking down at Dean in the illumination of the light. Yeah, he was definitely shaking. His forehead was covered in sweat and his nose was a bright angry red. And considering how pale the younger man was, Castiel wasn’t surprised when the words ‘Death warmed over’ sounded in his mind.

He held out a tentative hand, resting the back of it against Dean’s clammy forehead. _Shit,_ he was burning up. “Dean?” He moved his hand to Dean’s shoulder and shook it lightly, trying to get him to wake. “Dean.”

His response was a soft groan. Whatever Dean’s system was battling—it was far worse than the runny nose that Boston had dealt with.

Castiel slipped back out of the room, going into the nearby bathroom to grab a washcloth and soak it in cool water. He filled one of the plastic drinking cups with water as well, before hurrying back to Dean’s bedside.

Setting the cup of water aside, he gently brushed the washcloth along Dean’s forehead, making his hair stick up at odd angles. “Come on, Dean, wake up.”

It took longer than it should, but finally green eyes blinked open wearily and stared at him. Castiel got the feeling that Dean was looking, but not really seeing. 

“Hello, Dean,” Castiel whispered, continuing to wipe away the sweat on his brow. “You’ve got a fever. I’ve got some water here… I need you to sit up and drink some for me, okay?”

Finally getting his brain to work, Dean blinked. “Cas?”

“Yeah.” He sat down on the edge of Dean’s bed, and picked up the cup of water. “Sit up and take a drink, Dean.”

‘Sitting up’ turned out to be leaning up far enough that he could drink the water without choking. When he was resting back against the bed again, Dean groaned in agony. “Am I dying?”

“Probably,” Castiel replied. He attempted humor, to keep Dean from dwelling on how bad he felt. “It’s most unfortunate, as well. Hiring good help is a pain in the ass.”

Despite Castiel’s pause, there was no reaction. Dean just went back to shivering under the blankets. Another quick trip down the hall to the bathroom found a bottle of Tylenol, that would hopefully help break Dean’s fever. He refilled the glass of water while he was at it, and soaked the rag once more. 

If getting Dean to sit up the first time was hard, then the second time was monumental. Castiel had to force his own body between Dean and the headboard and hold him up while he nudged at his lips with the medicine. After Dean swallowed the pills, he let his head fall with a thud onto Castiel’s shoulders. 

“Don’t get you,” Dean moaned.

The words were soft enough that Castiel struggled to hear. “Hmm?”

In the midst of his fever, it was obvious that Dean was struggling to get his thoughts straight. “Just the nanny. Not Paul.”

 _Paul?_ Castiel frowned immediately. He couldn’t figure out how Dean would know that name. _Unless…God damn it._ “Dean…” 

“No, no, it’s fine,” Dean slurred as he pushed himself off of Castiel’s shoulders. “I’m not your favorite anymore. S’okay.”

“Let’s just get this fever down, okay?” A frown creased Castiel’s forehead. “We’ll talk about this later.”

Dean snuggled back into the bed, his eyes already closed. Unfortunately, his brain didn’t seem ready to shut up. “Guess I shouldn’t ‘try new things’.”

Castiel felt a cold chill roll down his spine at the words. He remembered the beginning of the week—practically a lifetime ago—and how it had felt to get Dean so obviously worked up. He had enjoyed it… _a lot_. When they had finally made it back to the condo, Castiel had locked himself in the master bathroom and jerked off to images of Dean on his knees begging Castiel to come on his face. It had been an earth shattering orgasm, and promised that the real thing would probably be a thousand times better. 

Standing in a rush, Castiel escaped from the room before he gave into the temptation to ask Dean what he knew about Paul. The regret he had been dealing with since his and Gabby’s ex-boyfriend weaseled his way back into their lives, reappeared like a burning pit in his stomach. He should have never given in. It wasn’t worth it—especially not if Dean had stumbled upon their drunken actions on the dining room table.

Unfortunately, he wasn’t the only one calling the shots. A fact made increasingly clearer when he reentered the living room downstairs.

Gabby and Paul sat snuggled on the sofa, with Boston sitting comfortably on Paul’s lap and playing patty-cake with the man. Any other day, the sight wouldn’t bother him, but with Dean’s words fresh in his mind it made his stomach roll. 

His wife glanced up, spotting him standing at the edge of the room. “Hey sweetheart. I ran into Paul on my way up. He wants to take us all out to see that new Disney on Ice show.” Her arm laid along the back of the sofa, her fingers dancing through Paul’s short brown hair.

Boston, suddenly uninterested in cooking meals for his sick nanny, turned to grin at his father. “It’s Frozen!”

“Dean is sick,” Castiel stated, fingers twitching nervously on the edge of his shirt. 

“That’s okay.” Paul smiled. “Gabby said it was Dean’s night off, so I only bought four tickets.”

Castiel let his eyes track back up the stairs. Even if he wanted to go, he knew that he couldn’t leave Dean alone when he had such a high fever. “You guys go ahead. I think I’m going to stay here and make sure Dean doesn’t get worse. He’s got a terrible fever.”

They both tried to protest, but Castiel got the distinct impression that they were putting on a show of their own. Half an hour later when they slipped out the door with Boston happily tugging their hands, he was reminded of why the relationship with Paul ended before. 

Maybe, despite Gabby’s argument to the contrary, Paul hadn’t changed much at all in the year that had passed.

**Notes for the Chapter:**

> ETA: hufflecas wrote two lines in this chapter. If you can pinpoint the two lines, I will send you a virtual cookie and give you a cameo in a later chapter. ;)


	8. Chapter 8

**Notes for the Chapter:**

> To all curious (I know there were a few), hufflecas' lines in chapter 7 were:
> 
> He couldn’t figure out how Dean would know that name. _Unless…God damn it._ “Dean…” 
> 
> “No, no, it’s fine,” Dean slurred as he pushed himself off of Castiel’s shoulders. “I’m not your favorite anymore. S’okay.”
> 
> “Let’s just get this fever down, okay?” A frown creased Castiel’s forehead. “We’ll talk about this later.”
> 
> (FYI: I hardly ever use the word "S'okay")

_Toddler Tip: It’s funny how someone can claim to love you but then say hurtful things like ‘walk’._

\---

When Dean started to feel slightly better Monday evening, it occurred to him that he had lost two full days from his memory. All he knew was that he felt sweaty and disgusting and wanted a shower. He shoved the sheets aside and tried to sit up, but his head was pounding and his stomach felt like it hated him. Every part of his body felt five times heavier than normal and just reaching an arm out to flick on the lamp seemed like too much work.

Once the lamp turned on, a figure sitting beside the bed jumped slightly. Dean frowned, trying to make his eyes focus. Castiel sat in a chair looking a little confused. He had a bright pink mark on his left cheek where his head had been resting against his fist while he slept. 

“Dean,” Castiel said softly, finally realizing where he was and what had startled him awake. He stood up, grabbing the nearby glass of water and holding it out to Dean. “Here, drink some of this.”

He let Castiel help him into a sitting position and sipped at the water before his stomach churned and he pushed it away. “What day is it?” he croaked.

“Monday.” Castiel looked down at his watch. “For another forty-five minutes.”

“Shit.” Dean tried to push himself up. “I’m sorry, Cas. Why didn’t you wake me up? I was supposed to work today.”

Laying the back of his hand along Dean’s forehead to check his temperature, Castiel shook his head. “I wasn’t going to make you worry about that while you were sick. Besides, it would have been pointless. You’ve barely been conscious enough every few hours to drinks some water and take some ibuprofen.”

He groaned, feeling useless and weak and… still really really clammy. “I need a shower.”

“You can barely sit up, Dean, how do you expect to stand long enough for a shower?”

_Fuck._ Dean pouted, wishing he was back home in Kansas for the first time ever. His mom and brother were always so good at taking care of him when he was sick.

Propping a few pillows up against the headboard, Castiel sat him back and told him to stay there before slipping out of the bedroom. Dean waited patiently, his head rolled back and throbbing gently. He felt so hungry. He could almost taste the soup his mom would make him and his brother when they weren’t feeling well.

“Okay.” Castiel walked back in, looking around the room. “Point out where your clean clothes are.”

Though Dean didn’t understand, he didn’t really have the energy to ask questions either. He pointed to his suitcase that sat on the dresser and watched Castiel pull out a clean pair of boxer-briefs, sweatpants, and a t-shirt. Once he had those things, he escaped back out of the room. The second time he came back, he moved to where Dean sat and held out his arms.

Dean stared at him like he was crazy. “What are you doing?”

“I ran a bath. Now let me help you in there before the damn thing gets cold.”

He generally hated baths—they took too long and he felt too much like he was soaking in his own juices—but at that moment, the thought sounded delightful. He curled one arm around Castiel’s shoulders and leaned heavily against him as he got out of the bed. 

They shuffled slowly out of the room and down the hall and Castiel couldn’t help but point out the fact that Dean seemed to have lost some weight. Considering Dean couldn’t remember the last meal he ate, it was probably true. 

Once they made it to the bathroom, Castiel shut the door behind them and let Dean rest against the counter so that he could shut off the water faucet in the tub. Dean watched him carefully and didn’t move. He felt so weak and his brain was moving like a slug. When Castiel stepped back in front of him, he grabbed the hem of Dean’s shirt and Dean frowned, but didn’t shove him away.

“What are you doing?”

Castiel slowly peeled the shirt off, maneuvering Dean’s arms out of the garment when he didn’t move to help. “You can’t take a bath in your clothes, Dean.”

The shirt hit the floor and finally Dean’s brain clicked on as he felt Castiel grabbing his pants. “Whoa.” He gripped one of Castiel’s wrists lightly. “I uh—I think I can manage?”

The look on Castiel’s face said quite clearly: _’Yeah right.’_ Instead of arguing though, Castiel stepped back half a step and motioned for Dean to go ahead.

Dean frowned. He did _not_ like the idea of being naked in front of his boss. Especially considering all of the moments over the past two months when he had imagined doing exactly that and jerked off to the images. He wasn’t gay, damn it, and he didn’t need to go getting a boner in front of Castiel when he felt weak and sick and just wanted a damn bath!

The thought of telling Castiel to leave the bathroom, died immediately on his tongue. There was no way he would be able to climb into the bathtub on his own. Taking a deep breath, he prayed that his dick would behave as he shoved his pants and underwear halfway down his legs. 

They got hung up on the drawer knob behind his knee and he bent down to unsnag them without thinking about how weak he was. Unfortunately, the lack of proper nutrition over three days meant that his equilibrium was way off. 

He tumbled forward, landing gently against Castiel who grabbed onto him to keep him from falling to the floor. 

With an exasperated huff, Castiel pushed Dean back so that he was standing once more, and bent down to help him step out of his pants. 

That was the moment when Dean’s body decided to betray him. It might have been Castiel’s light grip on his hip bone, keeping him in place, or maybe the brush of breath against his heated skin when Castiel knelt _right there_. Either way, his dick decided it wasn’t too sick to react. 

It wasn’t a full erection— _thank God_ —but he wasn’t completely flaccid any longer. Dean glanced down, praying Castiel wouldn’t notice. When blue eyes glanced up the length of his body and met his own gaze, Dean knew he wasn’t that lucky. Castiel didn’t say a word, though, just finished stripping Dean out of his clothes and stood back up to help him into the bathtub. 

As predicted, the water felt amazing. Dean took the offered soap and wash cloth and slowly washed away the grime of being sick. Castiel left him be and made sure that Dean knew he would be back in ten minutes to check on him. 

When the ten minutes were up, Castiel stepped back into the bathroom carrying a large mug in his hands. He kicked the door closed with his foot and moved over to sit on the side of the large tub. “Here, drink this.”

Dean took the mug, expecting tea or some other warm liquid concoction. Instead he was met with the warm aroma of chicken noodle soup. He literally moaned at the familiar smell, and quickly brought the cup up to take large gulps of the broth. It was delicious—much better than any canned version. 

When the soup was gone, he pulled the cup away and licked his lips. “Wow, Cas, that was amazing.”

“Thanks.” The older man smiled, taking the cup and placing it up on the counter. “There’s more downstairs. Once you’re settled back in bed I will grab you another cup full.”

“Good.” Dean looked down into the water. “I think I should get out now. The water is getting cold.”

Climbing out of the bath was a lot harder than climbing in—even if it did feel like some of his energy was beginning to return. After letting the water start to drain, Dean gripped onto Castiel’s arm as he pulled himself up to a standing position. Castiel left him like that, one hand resting on the wall, as he quickly grabbed a towel and passed it to Dean so he could dry off. 

Easier said than done. Drying his hair made his head hurt again, drying his arms required Castiel to hold onto his waist and keep him steady, and anything below his belly button brought on a wave of dizziness like he’d never felt before.

“Here.” Castiel took the towel and set it on the closed lid of the toilet and held his hands out to Dean. “Step out of the tub and I’ll dry off your legs.”

He followed the orders without objection—he was getting far too worn out to complain about modesty. Once his feet were out of the tub and resting on the soft bath mat, Castiel grabbed the towel and dropped down to his knees in front of Dean.

To keep his balance, Dean had no other choice but to rest his hands lightly on Castiel’s shoulders.

“You know,” Castiel spoke, dragging the towel slowly up Dean’s right leg. His voice was soft and his eyes were focused on the task before him - even if it should have been a simple one. “When I imagined seeing you naked for the first time, I didn’t add in the whole you-being-sick part.”

Dean stared down at Castiel’s hair, wanting to drag his fingers through the already wild strands. His brain was stuck on the words that had just been spoken, though. Castiel had wanted to see him naked? Despite the hints and the teasing, Dean had never seriously considered that Castiel honestly wanted him. Part of him was certain that all of it was a game.

He felt the towel moving up the back of his leg and over the skin of his ass. It wasn’t the sensation of scratchy cotton that made him gasp though. He watched in fascination as Castiel kissed lightly on the jut of his hipbone. _Fuck._ There went his dick again, making a valiant effort to get hard.

“I had imagined,” Castiel continued, his lips still dancing over Dean’s skin—skirting the edge of light brown pubic hair. “That the first time would be a bit rushed.” He brought the towel back around and started drying Dean’s left leg, his lips following suit and kissing across to Dean’s other hip. “Maybe it would just hit you one day—that you wanted me and you couldn’t wait another second to have me. You’d rip my shirt in your rush to get it off of my body and I would grab the belt loops on your jeans and pull you against me. So that you could feel _exactly_ how affected I was.”

“Cas,” Dean gasped. His right hand moved to dig into those dark strands of hair. They were just as soft as he had imagined.

“I wasn’t lying, Dean. I want you to try new things. But I left out one part.” He pulled back just far enough to look up and catch Dean’s gaze. “I didn’t mention how badly I wanted to be the one to teach you those new things.” 

The towel dropped, but Castiel’s hands slid up Dean’s legs in its place. One wrapped gently around Dean’s cock, holding the base of his stiffening erection. The other hand brushed over his balls, but pushed past—sliding over sensitive skin before the tip of a finger circled around his hole. 

Dean felt a shiver run down his spine at the contact. Followed a second later by a groan when Castiel’s tongue slid along the tip of his cock.

“Please, Cas,” he whimpered, unsure of what he was asking for.

Castiel moaned. “God you sound so sweet when you beg like that. Don’t even know what you want—just know that you _do_.” 

Dean could still feel Castiel’s eyes on his face, watching closely, but the pleasure was making Dean’s own eyelids grow heavy. The warm hands suddenly dropped away from his body as Castiel stood in front of him. Dean shifted his hips forward, trying to find the touch that had felt so amazing just a moment before. Instead, soft lips landed at the corner of his mouth. 

He blinked his eyes back open and stared in confusion. Castiel was stepping away. “What—”

“I’m sorry.” Dark blue eyes showed how truly sorry Castiel was. Dean looked down to see that the other man’s pants were also tented. “I can’t, Dean. I want you—God knows I do—but there are rules.” 

Castiel picked up Dean’s clean underwear and moved to help him step into the garment. He didn’t understand. The touch that had just been intimate was suddenly stiff and uncaring. “Rules?”

“Yes.” He moved on to getting Dean’s sweatpants pulled over his legs. “Gabby and I… we have rules, in regards to our relationship. Rules that sustain a happy marriage.”

_Fuck. Gabby._ “Shit, she’s going to be pissed. I didn’t mean to—” 

Castiel placed Dean’s t-shirt in his arms and met his gaze. “She won’t be angry. It’s just—” He sighed, looking away. “Anything that I can have, she can have. And vice versa. Any sexual relationship outside of the marriage has to be mutually agreed upon and…” he trailed off, but picked his words up again, “...happen while the other person is around.” When Castiel looked back up, he noticed Dean’s confusion over his words. “If I want to touch you, she has to be here, watching. To assure her that my heart will always belongs to her.”

“Right.” Dean summoned strength he didn’t know he had and pushed away from Castiel so that he could pull his shirt on. When it was on, he ducked his gaze. “Like with Paul.”

Though he looked like he wanted to say something on the subject of _Paul_ , Castiel simply nodded his head. “So… what do you think, Dean?”

“I think I’d like to go back to bed now,” Dean whispered.

**Notes for the Chapter:**

> For everyone suggesting that I didn't write the smut in previous chapters: THIS IS YOUR PUNISHMENT. Congratulations, you left poor Dean with blue balls.


	9. Chapter 9

**Notes for the Chapter:**

> So uh... this chapter _really_ got out of hand. And because of such I'm going to add bdsm to the tags. It's not intense, but there are definitely dom/sub undertones. 
> 
> Also: all het in this chapter. But it's leading up to good stuff so ENJOY.

_Toddler Tip: If you’re not sure if it’s a raisin, it’s probably not. Just throwed up._

\---

A week later, Dean was finally back to feeling normal—just in time for the announcement that he would be accompanying Gabby and Boston back to Los Angeles without Castiel. Apparently the man had another executive meeting the following week, and had to remain in New York for it, while Gabby had to get back for filming on her show.

Dean was actually okay with the prospect of spending time away from Castiel. After their moment in the bathroom—one of the few points he wished his fever brain had forgotten—Dean was ready to focus back on the reason why he had taken the job. _Bo._ He vowed to himself that he would focus solely on the boy’s well-being and let everything else fade into the background.

That was made easier by the fact that when they got on the plane, Boston wanted to sit next to Dean instead of his mother. Gabby shrugged, sitting down across the aisle and telling Dean that it would give her a chance to work on her scripts.

Dean spent two hours of the flight teaching Bo how to play Go Fish! which was definitely a lot more exciting than he had expected. They were both laughing so hard that even the flight attendants would stop and giggle with them every few minutes. Dean didn’t worry once about the plane crashing or the random turbulence—he was too focused on being cheated by a three-year-old.

When they finally landed and a car drove them back to the Novak house, Dean couldn’t believe how excited he was. At some point, Los Angeles had become _home._

They ordered pizza for dinner since the house was void of groceries and, by 7 p.m., Bo was crashed on the sofa. Dean carefully carried the boy upstairs to his bedroom and smiled softly as he tucked the blanket in just the way Bo liked. He left the door cracked open and moved down the hall to his own room, focused on catching up on his schooling while he had a few hours of peace.

Once he was engrossed in his studying, the time flew by. Before he knew it, it was a quarter to eleven and there was a knock on the door. Since it didn’t sound like the light tapping that Boston usually used, he figured it had to be Gabby knocking. “Come in.”

The door opened and sure enough, Gabby entered his room. She stayed just inside of the door and smiled at Dean. He really wished that he could have just an _ounce_ of the confidence she always showed.

“Hey Dean.”

He felt a shiver run down his spine. Being the center of Bree McKenna’s attention was _always_ nice. “Hi Gabby.”

“So Castiel has told me some secrets about you, Dean.” _He had?_ Dean felt a frown creasing his brow, but Gabby barely seemed to notice as she continued. “He says you’re a bit… curious about our lifestyle. And that maybe you aren’t quite ready to accept the part where he’s involved.”

The door closed softly behind her, but it barely registered in his mind. All he could focus on was her words and the fact that she was walking closer to his bed. “I, um… I’m not gay, Gabby.”

“Oh, I know sweetie.” She reached out, running a well manicured nail along his arm. “But I’m sure Cas has mentioned that he doesn’t consider himself gay either.” Leaning forward, she brushed her lips gently against his ear and whispered, “Liking a guy, and wanting to explore your own desires, makes you nothing more than curious.”

The synapses in his brain began to misfire. Bree _fucking_ McKenna was whispering in _his_ ear. His dick was stiff in an instant. Was he supposed to be talking? How did he make his mouth work again?

Gabby moved away, putting a few inches between herself and the bed. “I’m going to make you an offer, Dean. You have every right to either accept it or deny it, okay?”

It took a few moments of silence, before he nodded his head. His eyes were practically glued to her, memorizing the way that her auburn hair fell in soft curls around her like a halo. Her pink lips curving into a knowing smile. The flawless tan skin of her bare shoulders that could be seen thanks to her tank top… The tank top that hugged the swell of her breasts perfectly and reminded him of that damn magazine article he had enjoyed so much.

She reached out, gripping his chin and forcing him to look back up at her eyes. “I don’t like to sleep alone, Dean. I like to cuddle. I have Castiel’s permission to allow you into our bed so that you can keep me company for the next week.” 

His heart pounded at the thought. _In bed_ with Gabby. The possibilities of what could happen made his cock pulse again.

“There are rules, though, Dean.” While she continued to hold his chin, she reached up with her other hand and tapped the end of his nose. “You have to obey whatever I say or suggest. And if anything is ever _too much_ or _too uncomfortable_ you must use a safeword to let me know.”

Oh wow. He shivered. He wasn’t an idiot - he knew that establishing a _safe word_ meant they wouldn’t just be sleeping.

“Still with me?” she asked. He nodded obediently against her hand. “Good. One last rule. The most important of all.” Her finger trailed gently down his cheek. “You need to understand that Castiel and I did not hire you for any of this. Anything that happens in our bedroom will never have any effect on your job. Boston loves you, and we love how good you are with him, so think of this like Vegas: what happens in the bedroom, stays in the bedroom. Got it?”

He nodded once more. “Yes.”

Gabby’s eyebrow quirked. “Yes, what?”

_Fuck._ Why did that voice she used make his whole body shudder in excitement? “Yes, ma’am.”

“Do you agree to all of these rules, Dean?”

Dean licked his lips. “Yes, ma’am.”

“Good.” She dropped her hands but continued to hold his gaze. “What would you like your safe word to be?”

He took a few moments to think about that, trying to decide on what would be easiest to remember. In an instant, it hit him, and smiled. “Wichita.”

Gabby nodded, moving back towards his bedroom door. “Alright, Dean. Strip down to your boxers and meet me in the bedroom.” Her hands rested on her slightly swollen stomach. “Tonight you will give me a back massage, so I hope those hands of yours are as skilled as they look.”

She left his room after she spoke and Dean made quick work of his clothing. Probably a little _too_ quick. In his rush to kick his pants off, he fell flat on the floor with a thud. Whoops.

“Stupid pants,” he grumbled, kicking at them. 

When his feet were finally free, he stood back up and hurried out of his bedroom. He stopped at the edge of the hallway though, a few steps back from the open doorway that lead to the master bedroom. He had to get a grip. The way he was acting at that moment, he would come in his shorts as soon as he laid his hands on Gabby. 

How fucking _embarrassing_ would that be? He would probably use his safe word just to escape the shame. Taking a deep breath, he tried to force his body to calm down. Once he felt relaxed enough, he stepped forward and pushed the bedroom door open. 

Gabby was already laying on the bed, stretched out on her stomach in the middle of the bed. His breath caught in his throat and any hope of calming down was suddenly gone. She was _naked._ Why was that so damn hot? 

All he could see was curves and tanned flesh and _fuck_ it was too much. He reached down, ready to ease some of the pressure in his dick.

“Ah ah ah. I didn’t say you could do that.” Her voice made his hand immediately fall back to his side. Gabby smiled, her head resting on her folded arms. “Close and lock the door, then walk over here and stand beside of the bed.” He obeyed quickly and without hesitation. When he was standing beside her, she motioned with her head towards the bedside table. “Do you know what that is, Dean?”

Laying on the table, was a small leather band with a metal snap holding the perfect circle in place. He had a fairly good idea about what it was, but there was no way he was going to guess wrong in front of her. “No, ma’am?”

She smirked. “It’s a cockring, Dean. I’d rather not have you coming all over my back while you’re massaging me. So take that handy little strip of leather and wrap it around the base of your cock and balls.” 

_Shit._ To hear her talk so dirty was _almost_ too much. He reached out, picking up the cockring and holding it for a moment before meeting her gaze. “Here or... ?”

“Considering I don’t trust you not to jerk off in the bathroom… yes. Drop your shorts, put it on right here in front of me, and then cover yourself back up.” Ready to obey, he began shoving his boxer-briefs down to his knees. “No stroking, though, Dean,” she warned.

Despite her words, the urge to jerk off was _intense_. He made quick work of the task and once the cockring was in place, he regretfully pulled his underwear back up. His cock was still rock hard, but thankfully the urge to come right at that second had eased.

Without even second guessing the move, he looked up at Gabby for her next instruction. The next day he would probably laugh at himself for being so submissive, but the fact was… he did _not_ want to lose the opportunity to be in bed with Bree McKenna. And if he had to play a role for that chance, then so be it 

“The oil is already laying up here on the bed. You may sit straddling my legs so that you can reach well enough. I do _not_ want to feel your erection at any point during the massage. You may touch my asscheeks, but know that anything along my crack or pussy is off limits.” Her eyes held his to make sure he understood. When he nodded, Gabby smirked. “If you can make it through the entire massage without coming in your pants, I will jerk you off before we fall asleep. Got it?”

Dean nodded again, feeling like a bobblehead. And the thought of her touching his dick? _Holy fuck._ “Yes, ma’am.”

The suggestion of touching Bree McKenna’s skin was _intense_. The act of actually doing it… was mind boggling. The oil and the touching and the miles of tan flesh… it was all _way_ too much. 

Not to mention the task of making sure that when he leaned forward to rub his hands all the way to her shoulders and the back of her neck, he had to shift his hips up to make certain that his dick didn’t slide between the perky globes of her ass. But damn if he didn’t want to break the rules and feel that sensation.

His eyes kept flicking to the clock beside the bed, watching the minutes tick away as he wondered how long she would make him suffer. 

It ended up being all for nothing though. After seventeen minutes he massaged a particularly tense knot in her back and Gabby moaned. The sound was one of the most erotic things he had ever heard in his life. Dean hung his head in shame as his cock jerked and began to release spurts of come into the tight confines of his boxers. _Fuck._ He shuddered, hands sliding down and brushing over Gabby’s ass. His cock twitched again and he groaned, wondering what he had done in a past life to deserve such punishment. One gasp of pleasure from a woman and he was coming in his pants like he had just hit puberty.

When he blinked his eyes back open, Gabby was looking over her shoulder and watching him. A knowing smirk slid across her lips. “Just because you came, doesn’t mean the massage is over. Get back to work, boy.”


	10. Chapter 10

**Notes for the Chapter:**

> Couple things: 
> 
> 1) To all my wonderful readers, I'm doing a [Holiday Card/Fic Exchange](http://goo.gl/forms/jSnplOqoE1) and I invite you to sign up. Even if you live outside of the USA!
> 
> 2) The end of this will drive you nuts. Unfortunately, I might not be able to post another update until Sunday or Monday night. I'll shoot for earlier, but I really need to finish up my TFWBB fic. (all complaints can be sent to [this unsuspecting beta.](http://hufflecas.tumblr.com))

_Toddler Tip: The grocery store is a great place to bring shame to your family._

\---

It probably took longer than it should have for Dean to realize that something was wrong. If asked directly, he would probably blame it on his damn libido—and Gabby’s body. Despite everything, there was no denying that Gabby was hot and the sex was good (hell, great even) but, by the fourth evening, Dean was starting to feel a little uneasy.

He was all for allowing Gabby to dominate him in ways that he never would have dreamed about, but he was getting damn tired of her letting him come without any offer to touch him or fuck him. It was usually based on some impossible task. Things like: _’if you can make it thirty-six hours without jerking off, I’ll suck your dick.’_ and _‘lick my pussy and make me come twice—if you don’t come in your pants, you can fuck me.’_

Or, there was his personal favorite: _’wear this cock cage for the day; if you can prove you’ve earned it, I might let you come later.’_

When Sunday hit, he was out-of-his-mind horny and frustrated. It was more than a little obvious that Gabby had every intention of using him without giving him anything in return. Thankfully, Castiel was due to arrive back in Los Angeles that morning. Needing an escape, Dean jumped at the opportunity to pick his employer up at the airport.

Driving helped clear his head, even if he had to deal with the ever-present Los Angeles traffic. After parking the car in the short term lot, he climbed out and walked into LAX with a hop in his step. It was a bit surprising how much he had missed Castiel. Things just weren’t the same without him around.

He checked the screen for arrivals and smiled when he saw the flight from LaGuardia and a flashing ‘ON TIME’ beside it. _Good._ Finding a bench near the baggage claim, he sat down and shot a text off to Castiel about his location before opening a random game application to kill time. 

Thirty minutes later brown leather shoes stepped into his line of sight and a deep familiar voice said, “Hello, Dean.”

Dean’s heart skipped a beat as he looked up into those crystal blue eyes. “ _Cas._ ” He tucked his phone back into his pocket and quickly stood, reaching out to hug the older man. 

When Castiel’s familiar touch and comforting scent wrapped around him, the stress and frustration from the previous week finally evaporated. Dean snuggled just a little bit closer, eyes slipping closed and lips drifting over the skin above Castiel’s collar.

For his part, Castiel let the hug deepen without complaint. He could obviously tell that something was wrong, though it was hard not to. Dean felt soft lips brush along his ear before Castiel whispered, “What’s wrong, Dean?”

It was those three words that broke him. He gripped tight onto the back of Castiel’s shirt and buried his face against his shoulders as tears quickly began to fall. It hadn’t been obvious until he was back in a warm familiar embrace, but everything that Gabby had put him through had drained him both emotionally and physically. He wanted to wanted to give Castiel an answer, he really did, but couldn’t find the words or the strength to speak.

Castiel held onto him and let him cry for longer than was probably appropriate—considering they were in the middle of the airport. When he finally pulled back, it was only after Dean’s tears had started to dry. Strong hands cupped Dean’s face as Castiel held his gaze. A sad smile tugged at his lips, and then he was leaning forward. He didn’t give Dean a chance to argue or make excuses or back out—he just held him firmly as he claimed his lips with a toe-curling kiss. If Dean expected demanding—which he kind of did, after the week with Gabby—it wasn’t what he got. Though the kiss was persistent, it held the same amount of comfort as the hug they had just shared. 

It almost made him want to cry again. 

When they broke apart, Dean couldn’t help but pout. He didn’t even care that he had just kissed a guy in public—fuck everyone else’s opinions. All he cared about was kissing Castiel again… so he did.

The second time Castiel pulled away, he chuckled and kissed Dean’s nose. “For what it’s worth, I missed you too.”

“Doesn’t even begin to describe it,” Dean whispered.

“Yeah. Let me grab my bag and we can talk in the car.”

When they finally made it out to the car, Dean got into the driver’s seat and laid his hands on the steering wheel but didn’t start the engine. After Castiel buckled his seatbelt, Dean turned to look at him, still fighting with his emotions. “I’ll drop you off at home, but I think I’m going to find a motel for the night. I had to work yesterday, so Gabby gave me tomorrow off in exchange. I think I just need a break.”

Castiel was watching him closely, concern knitting his brow. “A break from me?” Dean bit his lip and quickly shook his head. “Boston?” Again, no. Understanding flashed in his eyes. “Gabby.”

It wasn’t a question, but Dean nodded anyways. He waited another second, before starting the car and putting on his own seatbelt. 

They both remained quiet as they fought through airport traffic. Dean noticed Castiel messing with his phone, but didn’t bother with asking what he was doing. When they made it to the 405 heading north, Castiel finally put his phone away and spoke up. 

“Take the 10 towards Santa Monica.”

He gave no explanation, causing Dean to frown. “Why?” That route would take them west, towards the ocean, instead of northeast, towards Castiel and Gabby’s house.

Castiel glanced at him quickly, a small smile on his face. “Because that’s where our hotel for the night is.”

\---

Dean protested exactly four and a half times before Castiel told him to shut up because it was doing absolutely no good. When they arrived at the posh hotel overlooking the ocean, Dean tried for one last argument.

“What about the… _rules_?”

The car was parked under the mezzanine by the lobby door, and Castiel’s hand was already on the door handle ready to open it so he could climb out and check them in. He looked back to Dean, eyebrows raised. “Has Gabby followed those rules?”

Dean had no idea what the fine print on their ‘rules’ was. What qualified as an act that needed to take place with the other party around? If it was full-on penetrative sex then Gabby hadn’t even came close to breaking the rules, just dangled it in front of Dean like a treat on the end of a stick. _Always unreachable._

While he contemplated all of those things, Castiel didn’t wait for his answer and jumped out of the car to go inside the hotel. Dean watched through the windows as he checked into the room he had apparently reserved. It took a few minutes, but finally he exited the lobby and climbed back into the car. “Park over there on the left side of the building, she said that’s the easiest access point to our room.”

Dean parked the car in an open spot and shut it off. When he looked to his left, he had a clear view of the pacific ocean. “I don’t have any clothes.”

“I have some clean things you can borrow. Come on.” Castiel climbed out of the car, but stopped suddenly and leaned down to look in at Dean. “Fuck… I’m sorry, Dean. I’m being just as controlling as she probably was. Tell me right now: do you want me to stay or not? Because I won’t be upset if you just want to be alone. You can enjoy the room and I’ll get one for myself on a different floor.”

It was an out, laid right there in front of him. If it had been Gabby, instead of Castiel, Dean had a feeling things would be different. Even her ‘safe word’ seemed like a load of shit now that he thought about it. It was great in theory, but the psychological pressure to perform and please her had rendered any and all escapes useless.

Dean got out of the car without hesitation and locked the doors. He stepped towards the hotel entrance and turned, holding his hand out to Castiel.

If whatever was about to happen was anything like what had taken place with Gabby, then Dean had a feeling he was going to need to find a new job.

They took the elevator to the fourth floor and Castiel held on tight to Dean’s hand as he lead the way to room 414. The place was nice, as would be expected for a waterfront hotel in Santa Monica, and the door opened to a room furnished with a large king size bed, a table with two chairs, and a dresser with a flat screen tv sitting on it. Dean paid little attention to the furniture as he crossed the room and opened the balcony door. 

The view was even better from their room.

He stood out on the balcony, leaning against the white-washed wooden railing and watching the waves. After leaving his bag on the bed, Castiel walked out as well, standing directly beside Dean.

“I want you to tell me everything that happened this week while I was gone, Dean.” Castiel turned towards him, running his thumb softly down Dean’s arms. “I want to hear it all. But first… I think I need to explain a few things to you. I think you deserve to know exactly why Gabby’s actions were the initial reasoning behind us creating rules.”

Castiel mentioning their ‘ _rules_ ’ again made Dean’s stomach twist. Whatever he had wanted from their night alone together—he had a feeling it wasn’t going to happen because of those damn rules.

Pulling him from his thoughts, Castiel laid his hand over Dean’s, letting their fingers intertwine, and leaned forward to kiss his neck. His lips burned a path to Dean’s ear, and his voice darkened as he whispered.

“Because despite all of that talking, Dean, at some point tonight… we’re going to mess up those sheets and you’re going to fuck me until we’re both screaming. I guarantee it.”


	11. Chapter 11

**Notes for the Chapter:**

> /liar about posting schedule

_Toddler Tip: The moment your scream is so high pitched you startle a stranger._

\---

There was something to be said about the sight of tan flesh spread out over white cotton sheets. And having a six foot tall man spread out, hands tied securely to the headboard, ready and willing to be completely devoured, caused a rush like no other.

“Are you sure you want this?”

The answer was an emphatic nod of the head.

Gabby smirked. It was hard for him to talk with a ball gag in his mouth. “Pretty little pet, always ready to please me, aren’t you?” She moved one knee onto the king size bed and reached out to brush her fingers through light brown hair. “I think it’s time for some stimulation—how does that sound?”

He nodded again, and she could easily see the pleading look in his eyes. She stood back up and moved to the dresser, quickly grabbing a bottle of lube and one of her favorite toys. “I know you probably want me to touch your dick, pet, but I don’t think you’ve earned that privilege.” Climbing onto the bed, she knelt on her heels and tapped his knee with her free hand. “Knees bent, legs spread. No shifting or moving.”

He followed her orders, his eye watching every move she made with just the slightest hint of fear. After lubing her index finger, she circled the rim of his hole with a feather light touch and watched with pleasure as he fought the urge to grind his hips. 

That was the only teasing she allowed. Her movements quickly changed to methodical prepping as she stretched him open enough to allow the toy easy entrance. When Gabby concluded that he was ready, she withdrew her finger and slicked up the small vibrator. 

As soon as she pushed the toy inside, she watched as his body visibly tensed. Looking up to hold his gaze, Gabby watched recognition dawn on him. And then she turned the vibrator on.

Finding his prostate was as easy as twisting the end of the toy and watching his hips jump when she hit the right spot. She smirked. “Feel good, pet?”

His eyes were squeezed shut and his dick lay hard against his stomach, a couple drops of precome leaking from the tip. When Gabby didn’t receive a proper answer, she turned the vibrator off.

Not even the ball gag in his mouth could prevent his scream of frustration from being heard. Gabby slapped the bare skin of his thigh. “I _asked you_ a question. Does it feel good?”

Eyes back open, his head bobbed in confirmation of the answer.

“Good, pet.” She turned the toy back on, slapping his leg again when he shifted his hips into the pressure. “No moving!”

She had seen him come enough in recent days to know when his body was on the edge. When the signs became obvious, she reached up with her left hand and squeezed the base of his cock, abruptly cutting off his orgasm. He yelled again in frustration.

“Oh I’m sorry, did I say you were allowed to come? I don’t think I did.” She dropped her hand away, waiting another couple minutes for the prostate stimulation to bring him back to the same spot. Just like before, she stopped his climax with a tight squeeze. 

His whole body writhed in aggravated need. 

“Poor pet. I think you’ve been spoiled lately. You’re probably due for a new lesson.” Gabby turned the vibrator off, but left it firmly pushed inside of his ass. Turning to her right, she grabbed onto his ankle and stretched his leg out, quickly tying his left leg down before repeating the move on his right leg. 

He was spread eagle, tied down with a leaking cock and a vibrator in his ass… providing pressure but not quite enough to get him off. 

Climbing off of the bed, she smirked. “It’s almost dinner time. I’ll be back in a few hours. If I come back and you have come drying on your stomach, I’m going to get out the paddle and you won’t be able to sit for a week.”

Two hours later, she was almost finished cooking dinner when the front door opened. Gabby turned her head towards the door and smiled when she saw her husband stepping inside. “Hey sweetheart, how was your day?”

“Good.” Castiel let his bag drop onto the floor in the foyer and hung up his coat, before walking up behind her. His arms wrapped around her waist, brushing just beneath the edge of the tank top she was wearing. “It smells delicious.” He kissed along the back of her neck. “I saw the Chevy parked out front. Where is he?”

She wiggled her hips back against him, finding it hard to concentrate on cooking. “He’s a little tied up. I’m teaching him a lesson.” There was a pause before Castiel drew away. Gabby glanced over her shoulder, her eyebrows raised in confusion. “What’s wrong?”

Castiel frowned, his eyes darting towards the hallway. “You promised you were going to go easy on him, Gabby. How long has he been tied up?”

“I don’t know.” She shrugged, brushing off his concern and looking back at the roast that was nearly done. “A couple of hours. He’s fine.”

“ _What?_ You’ve left him alone for a ‘ _couple of hours_ ’? Did you leave the bell with him? Does he have a way of safe wording?”

Gabby rolled her eyes. “No. He’s not a pussy like you, Cas. He stays in the mindset and he doesn’t need a quick out. He’s happily accepting his punishment!”

“How do you know he doesn’t need an ‘out’ if you aren’t in there watching him? Damn it, Gabby, we talked about this.” Castiel turned, cutting off the argument as he stormed out of the kitchen and towards the stairs.

\---

Castiel sat in the chair beside the bed, body stretched forward as he held his head in his hands. Thinking about the way that Gabby used power and dominance without any sense of control always left him feeling emotionally drained.

Apparently, despite the time that had passed since the first time Gabby went overboard—despite the multiple rules that they had established—she was still having issues with seeing where the limit was. He was running out of options. He loved his wife, and he wanted all aspects of their lives to be safe, healthy, and loving, but making her realize the necessity for that in the bedroom as well was difficult.

Raising his head, he looked across to the man perched on the large bed before him. “I’ve talked to a psychiatrist about her actions before. He seemed to think that all of this is a result of her career. Gabby has so little control over Bree McKenna that when she finds an outlet like domination she goes too far and doesn’t know when to stop.”

“That’s not really an excuse,” Dean replied. He fidgeted where he sat, right hand rubbing nervously along his left wrist. “I mean… I know I’m new to all of this shit, but to throw yourself over and allow someone else complete control requires a hell of a lot of trust. And how do you trust someone when you know they’ve repeatedly fucked up?”

“I know.” Castiel looked across the room, eyes unfocused. “I thought the rules had changed things. How out of control could she get if she wasn’t allowed to play like that without me nearby?”

Dean snorted in answer.

Castiel continued. “When we were in New York—when Paul said he wanted to meet back up —I knew that was going to be the true test. Her domination game that day, leaving him tied up in the bed for hours without a way to call if he needed to get free, _that_ was the moment that ended our relationship with Paul. So for him to want to try again, and for everything to go okay when the three of us were together—I took that as a good sign.”

“Yeah,” Dean let out a humorless laugh. “She _really_ changed. I mean she made it a whole twelve hours before she had me tied up in the same fucking way.” He ran a shaky hand through his hair, making the dark blonde strands stick up in various directions. “I’m such a fucking idiot. If I wasn’t so fucking infatuated with nailing a superstar, I would have never given in to her demands. God… I miss good old _normal_ sex. Guy gets off, girl gets off, everyone leaves happy.”

Dean’s words created an ache in Castiel’s heart. It wasn’t fair to the kid to put him through so much and expect him to stay—to _want_ to develop some kind of relationship with Castiel. Dean had never been with or had feelings for a man before, which meant there was a very strong possibility that whatever was between them was also unhealthy.

Sometimes making the right decisions for the good of others… _sucked._ Castiel wanted Dean. He wanted to enjoy every one of the feelings between them. But he wouldn’t risk hurting Dean because of his own desires.

“You’re right, Dean. Believe me… when I hired you, I never expected or wanted any of this to happen. I just wanted someone trustworthy and fun loving to watch over my son.” He paused, trying to find the right way to say his next words. “I know that there is a… considerable attraction… between you and I, but I’m fully prepared and capable of taking a step back for your own good. I don’t want you to do something else that you will end up regretting.”

When he looked up, he saw the frown creasing over Dean’s brow. Castiel’s heart sank a little and he took a deep breath, preparing for rejection.

A small smile tugged at the edge of Dean’s lips. “Excuse me? I’ve learned my lesson. And if you think you’re getting out of letting me fuck you _that_ easily…”


	12. Chapter 12

**Notes for the Chapter:**

> Special thanks to hufflecas for spectacularly imparting her blowjob perfecting skills on this. (ie: she writes good blowjobs, yo)
> 
> Of course then she made my writer senses pouty so I finished the end of this without showing her and I may be a 2-year-old when I don't get my way. MEH. Sue me.

_Toddler Tip: Asked for dessert. Was told oatmeal is dinner and dessert in one. I need to hit._

\---

There was no real easy segue from discussing Gabby’s horrible sex antics to having sex themselves, so Castiel suggested the idea of walking around the neighborhood and finding a good place to eat dinner. Since Dean’s nerves were a giant bundle in the pit of his stomach, he was completely okay with doing something— _anything_ —else for the time being.

Two blocks from the hotel, they found a trendy café with live music and a patio overlooking the water. They sat across from each other and before Dean even had a chance to look at the menu, Castiel spoke up and ordered for them. When Dean gave him a ‘what the fuck was that for’ look, Castiel leaned over the table and lowered his voice to answer.

“I didn’t want you to overindulge and feel too full later. No need for cramping while you’re making me scream.”

It wasn’t much—just the slightest hint of what was to come—but it was enough to cause a shiver to run down Dean’s spine. His nerves had started to dissipate as soon as they were out of the hotel room and sex was no longer ‘expected’. Now, sitting in a restaurant full of people, hinting and whispering about sex was naughty and exciting.

It was one of the benefits of Castiel being older and more knowledgable. He could read Dean’s emotions and knew how to ease the tension of certain situations.

The waiter walked back to their table and set down two glasses of white wine before informing them he’d be right back with their meal and walking off again. Dean stared at the glass before him for a second and then raised his eyebrows at Castiel. The older man was already taking a sip from his own glass and merely shrugged.

Apparently the whole _under twenty-one_ thing was not such a big deal when ordered with the right amount of authority. Dean picked up his wine glass tentatively and took a sip. The fruity tones that hit his tongue were not what he was expecting. “Are you trying to get me drunk, Cas?”

“Unless you’re an extreme lightweight one glass won’t get you drunk. But it will help ease the tension in your shoulders.” Castiel smiled, setting his glass back down. “You know we don’t have to do anything tonight, right Dean? I would never be offended or hurt if you decided to change your mind at any point in this process.”

Before Dean could answer, their food was brought to the table and the waiter asked if they would be needing anything else. Castiel shook his head and when the man walked off, Dean spoke up. “I know, Cas. And I know that you respect the word ‘no’ a lot more than Gabby did. That’s not what I’m nervous about.” He picked up his fork and poked at the shrimp and crab salad before him, before frowning. “I’m worried about doing something stupid and disappointing you.”

“Well,” Castiel mused, “I can’t promise you’ll be perfect or that you won’t make mistakes, but none of those things will disappoint me. The only thing that could possibly disappoint me would be if you forced yourself into a situation you weren’t comfortable with, just because you thought it would make me happy. That’s not how this is supposed to work, Dean.”

Dean nodded. “Okay.”

“Good, now… let’s talk about something more interesting. Have you ever had a desire to go surfing?”

\---

When they finished dinner the sun was just beginning its slow descent over the horizon, so they decided to walk back to their hotel along the beach. Castiel had been right—the wine had helped just enough to ease Dean’s stress and worries. He didn’t even care what people might think as he grabbed onto Castiel’s hand while they walked. Fuck people. It wasn’t any of their business anyways.

When they were halfway back to their hotel, Castiel slowed before switching direction and tugging at Dean’s hand to follow. He did, albeit a little confused. That is, until he noticed where Castiel was headed. 

 

Along the beach in front of a different hotel were several shade tents housing beach chairs. Since it was after sundown, they were deserted. Castiel picked the tent farthest from the hotel and pulled Dean inside before dropping the front flap behind them. 

“What are you—” 

Dean’s words were cut off by a sudden kiss as Castiel grasped onto Dean’s belt loops and tugged him closer. Their hips met and there was no denying the stiff erection beneath Castiel’s slacks. Dean relaxed into the kiss, hands awkwardly landing on Castiel’s waist and staying put. He didn’t know where or what to touch.

That didn’t slow Castiel down at all, though. He tugged at the edge of his own dress shirt that Dean had borrowed to wear to dinner and groaned into the kiss as his fingers brushed up Dean’s back. 

It felt good, and Dean’s cock was definitely taking notice. 

“Mmm,” Castiel purred. His kiss moved away from Dean’s lips and down to his neck. “I know you were pretty out of your mind with that fever… but please tell me you remember our time together in the bathroom in New York.” 

How could he _not_ remember that? Dean grunted, feeling his dick twitch in his pants. “I remember. You got me all wound up and then said you had to stop because of those damn rules.”

“Well, the rules be damned.” Castiel palmed Dean’s erection through his pants and bit gently at the dip of his shoulder. “Right now I’d like to test out that 19-year-old refractory period of yours.” 

Confused, Dean watched as Castiel slid down his body and knelt before him in the sand. When he leaned forward to mouth at Dean’s dick through his pants, Dean’s head fell back and he moaned. “Fuck, Cas.”

“Later, hot shot.”

His fingers worked in a flurry to undo Dean’s pants and shove them down around his ankles, followed quickly by the slate gray boxer briefs that Dean had put on that morning. It was such an overwhelming rush that Dean felt his head spin and had to reach out to grab the corner post of the tent—the only thing nearby that he could grab on to other than Castiel.

Once Dean’s cock was free, Castiel didn’t hesitate at all to wrap his lips around it and _suck_.

“Holy shit,” Dean said, feeling his legs wobble like jelly at the intense pleasure that quickly ripped through him. “Warn a guy!”

There was no reply. Castiel quite literally had his mouth full. 

Dean found himself torn between watching the amazing sight before him, and closing his eyes to enjoy every single overwhelming sensation. His free hand reached out, grasping onto Castiel’s hair and holding him in place as Dean shifted his hips. 

Dean buried his fingers in Castiel’s hair and the older man responded by humming around Dean’s dick. The vibrations reverberated around his cock and it was all Dean could do to not cry out. Castiel flattened his tongue along the bottom of Dean’s shaft, and licked to the tip before swallowing all of him down again. Dean had had his dick sucked before, but it had never been like _this_. If one thing was sure, it was that Castiel knew his way around a hard cock.

Once Castiel set a steady pace of bobbing his head up and down the length of Dean’s cock it was all Dean could do to keep his grip on that tent post and not go hurtling through the canvas wall. He chanced a look down at the dirty and hot scene in front of him and by chance Castiel looked up and met his gaze. Even half naked and coming apart Castiel could still read Dean’s every sign. When Dean’s hips began to quiver and stutter Castiel tightened his hold on Dean’s hips and hollowed his cheeks. Dean came with a groan, just barely remembering to not pull at Castiel’s hair too hard. If Dean hadn’t just shot half his brains out through his dick he may not have made it through watching Castiel actually swallow his come. 

Castiel pulled off of Dean’s dick, wiping a stray drop of come from the corner of his mouth. He sat back on his heels and looked up at Dean, a content look on his face. “Are you feeling better?”

The fact that he was expected to reply after _that_ was a little too much. Dean managed to nod his head, but that was the extent of it.

Amazingly, an answer was spoken, but it wasn’t from Dean _or_ Castiel.

"Uhm, excuse me?"

They both turned to look at the front flap of the tent, frowns on their faces thanks to the sound of a female voice. Dean looked back down to Castiel, trying to silently communicate ' _what the hell do we do?_ '

The woman spoke up once more. "My name is Helena. I work at the Inn. I know someone's in there... I could hear you. If you don't leave now, my boss is going to call the cops."

Castiel quickly sprung into action, tucking Dean's cock back into his pants and standing. He brushed the sand off of his own slacks and made sure they both looked presentable, before pushing the flap aside and stepping out from the tent. Dean followed closely behind, feeling more than a little anxious over being caught.

"No need for that, we're leaving. Sorry for the trouble." He held his hands out in front of his body in the universal symbol of surrender. "I swear we didn't disturb anything but the sand, ma'am."

She rolled her eyes. "It's fine, you aren't the first and won't be the last. Just hurry up and go."

They continued walking in a rush down the beach towards their own hotel. Once the tents were out of sight, Castiel stopped, leaning forward against his knees as he started to laugh. "Dean, your middle name must be Trouble."


	13. Chapter 13

**Notes for the Chapter:**

> **Top Dean/Bottom Cas!**
> 
> Apologies for the delay in this. Seriously. I hit a wall, and I had to work too much and I really have no excuse. The boys were just being BUTTS.
> 
> Thanks to [coplins](http://archiveofourown.org/users/coplins/pseuds/coplins) for letting me borrow Katie from her [story.](http://archiveofourown.org/works/2280492/chapters/5027447) :)
> 
> Also thanks to hufflecas for getting Dean in the tub. LOL

_Toddler Tip: Love bath time. It always gives me that much needed second wind._

\---

After the experience in the tent, Dean wasn’t sure what he was expecting when he arrived back at their hotel room. His body was definitely still vibrating with desire, lust, and need - and if Castiel had suggested stripping down and going at it right after they walked through the door, he would probably have said yes. Maybe with more nervousness than eager anticipation though. Dean was still certain he was going to mess everything up.

Castiel, however, had other plans. After they were settled into the room, he peeked his head into the large fancy bathroom and leaned back out with a smile on his face. “I love nice hotels, they always meet and exceed my expectations.”

Since he had no idea what Castiel was talking about, Dean shrugged and walked further into the room, kicking off his shoes. “Yeah, sure.” 

"By which I mean," Castiel continued, taking off his own shoes and jacket, "they almost always have bathtubs comfortably large enough for two people." He disappeared into the bathroom, and Dean heard the telltale rumble of the faucet.

He didn’t need to be told twice. Making a beeline for the bathroom, as he rounded the corner Dean was greeted by the sight of Castiel’s back as he bent over to slide off his pants. When he stood up, he was completely naked. He kicked his pants away from the tub, across the room, and fixed Dean with a stare. He kneeled over once more, this time to dip a hand in the water, that was slowly rising. 

Dean noticed the steam already filling the small room. He closed the door behind him. “How’s the water?” he asked as casually as he possibly could. 

“Almost perfect,” Castiel replied, carefully stepping into the bathtub. “It’s just missing one thing. Come here.”

Dean’s hands pulled his shirt over his head and pushed his jeans away and without him even realizing it, he was naked. He fought back the urge to feel self-conscious as he stepped carefully into the tub, easing down in the free space across from Castiel. 

Of course, now that he was sitting in a bathtub with another man… Dean had _no_ idea what his next move should be.

Grabbing a bottle of soap and washcloth from the side of the tub, Castiel poured an ample amount of soap on the cloth and stretched Dean’s right leg out so that it rested gently against his lap. Then, much to Dean’s chagrin, Castiel began slowly _bathing_ him. Suddenly he felt like a little kid in his momma’s bathtub. Except… maybe not. Because despite the awkwardness, there was an underlying tingle of _sexy._

“Dean,” Castiel spoke, his voice as gentle as his touch. “Tell me about your first time.”

The question immediately gave him pause. It had been almost three years since his first time, but he could very clearly remember it. It wasn’t a stretch to call the whole experience incredibly _awkward_. At sixteen, he thought he knew everything - after all, the locker rooms at school were full of stories about how amazing sex was and which technique worked best to keep your dick hard longer. And he had seen enough porn to figure out the basics and then some. 

He was stupid and naive, and that was probably why he was so nervous at the prospect of fucking Castiel. It was yet another new experience that he really didn’t have knowledge of and… yeah, he was going to make an utter fool of himself.

“Beginning of junior year, I went on a few dates with this girl name Katie Leboux. I was never the most popular kid in school; I had a group of five or so friends and that was it. Katie was the same way. She was pretty and smart, but in a very girl-next-door kind of way. Fuck, she was hot. Her hair was this pretty chocolate brown color, and she liked to wear it in a braid down one side. And her eyes - I think I first noticed her because of her eyes. They were amber colored, sparkling with flecks of gold.”

Dean stopped talking, lost in the memories. His heart still hurt at the thought of Katie blinking back tears in those pretty golden eyes. He had done that. He had ripped away the innocence of a smart girl that wasn’t quite ready. 

Castiel’s hands stilled. He dropped the cloth into the water and reached out for Dean’s wrists. Dean found himself being pulled closer to the older man, until he was straddling his lap, sitting gently on Castiel’s thighs. 

“You know,” Castiel whispered, fingers brushing lightly along Dean’s face. “No one is very good their first time. I lost my virginity with a guy. I had no idea I even liked women until I met Gabby.” Though Castiel had asked about Dean’s first time, he obviously sensed that the memories were hard for Dean to face. So he kissed Dean’s nose and shared his own story. “I was living in Phoenix with my brother Zeke. His best friend had a very obvious thing for me. Benny. God he was an asshole. Have you ever heard the term ‘topping from the bottom’?” When Dean shook his head, Castiel let out a humorless laugh. “Well that was Benny. Even though he agreed to let me fuck him and talk me through the steps - he spent the whole time critiquing everything I did and getting angry with me when I messed up. I ended up losing my erection and he just rolled his eyes and fucked me instead.”

“Oh.” Dean shifted, eyes down to avoid Castiel’s as he realized… that was everything he was worried about happening. That he would be so ridiculously bad at topping, Castiel would mock his efforts and ask him to stop.

A finger pressed gently on his chin, raising his head back up so that his eyes met Castiel’s. “I would _never_ do that to you, Dean. I don’t expect you to be perfect. That’s why I told you that story. So that you would realize just how easy it is to be horrible - and still move past it and be better for it.”

“I’m not better for how I treated Katie…”

“Yes, you are. Because you would _never_ treat someone like that again, would you?”

“No.” Dean adamantly shook his head. “Katie taught me a valuable lesson about consent. That even words like _‘yes, I want this’_ aren’t always honest. If I had just looked into her eyes, I would have seen how much she didn’t want any of it.”

\---

With every minute that he spent with Dean Winchester, Castiel knew one thing was true: he was in too deep.

The real world would soon come knocking and he wasn’t ready for it. He wasn’t ready to face Gabby and the fact that it didn’t matter how many quiet hours he spent with Dean - he was still married. Still more than ten years older than the boy.

“Mmmm.” Okay, ‘boy’ was _definitely not_ the right word. Not when Dean was gently pressing two slicked up fingers into his hole. “That’s good,” Castiel gasped. He was on his knees and elbows on the bed, Dean settled behind him and showing signs of being the best damn student ever. Castiel tried not to get too lost in the feelings as he continued talking Dean through the steps of preparation. “Now, every person is different. I’ve been with a guy who, after two fingers, was ready and begging for cock, and I’ve also been with a guy that wanted to be stretched as much as possible and then brought to climax before he let you fuck him.”

Dean moved his fingers, twisting and curling them like Castiel was a science experiment that Dean was ready and willing to figure out. 

By complete happenstance, his fingers brushed over Castiel’s prostate and _ohholyfuckingshit_. He hadn’t even gotten to the part where he told Dean how sensitive his prostate was and just the slightest brush made Castiel keen with pleasure. Apparently there was no need, because the little shit had to be smirking as he repeated the touch and Castiel was not ashamed to admit that he was humping the pillow beneath his hips. “God damn it, Dean, stop that!”

“Why?” Dean challenged. 

Oh yeah. Castiel couldn’t see it, but there was definitely a smirk on Dean’s face, of this he had no doubt. “Because, as I was just explaining—”

 _SHIT._ Dean’s fingers did that _thing_ again, and Castiel’s whole body shuddered. He was going to let go way too soon if Dean didn’t fucking stop it.

Lips landed on Castiel’s lower back as Dean resumed pumping his fingers gently. “I bet you’re somewhere in the middle,” Dean said, voice just the slightest bit cocky. “You aren’t ready after just two fingers—” To punctuate his words, he slowly pushed a third finger inside and _damn it_ how did he learn so quickly? “—but you don’t want to come like this. I bet you like to be brought right to the edge, don’t ya, Cas?” He curled all three fingers, rubbing in a sporadic rhythm over Castiel’s prostate. It was too much, but never quite enough. He moved his hips, pressing his cock down against the smooth cotton pillowcase before moving back against the probing fingers in his ass. “Get all wound up and ready to let go, only to have me pull away at the very… last… second.”

With one last long tantalizing stroke over his prostate, Dean pulled his fingers free and leaned away from Castiel. “I hate you,” Castiel grunted, face practically buried in the sheets as he tried to still his rapidly beating heart. He was _soclose_.

“Mhmm,” Dean replied. “What next, teacher?”

He waved an arm in the general direction of where the lube sat beside a still wrapped condom. “Condom. Lube. Fuck. Me.”

Castiel caught only glimpse from the corner of his eye, as Dean followed instructions and sheathed with the condom, before applying an ample amount of lube. He stopped there, though, and didn’t follow the _most important fucking part of the instructions._

“Dean?” Castiel asked, trying to think through the fog of need in his mind and figure out why Dean wasn’t moving or pressing inside of him yet.

“I, uh—” It didn’t take much to hear the panic rising up in his voice, causing Castiel to roll halfway over and look at Dean in concern. Dean forced a shaky nervous smile and continued. “I know it would probably be easier like this… but you’ve got my head stuck on my first time and I just…” The smile faded and he stared directly into Castiel’s gaze. “Can you lay on your back? So I can see your eyes?”

Castiel realized immediately what was wrong. In order to know that Castiel really wanted what was happening, Dean needed to be able to see the consent in his eyes. He rolled onto his back without hesitation, keeping the pillow beneath him to help elevate his hips. “Of course, Dean.”

Though the smile on Dean’s face still held a bit of nervous energy, he seemed to happily be back in the right headspace as he leaned over Castiel to kiss him.

When Dean pressed his cock slowly inside for the first time, Castiel’s first instincts were to let his eyes slip closed and enjoy the familiar burn. He fought past it, keeping his gaze locked with Dean’s.

The depth of those green eyes was going to be the death of him.


	14. Chapter 14

**Notes for the Chapter:**

> *holds up tarp to avoid tomatoes being thrown at me*

_Toddler Tip: Wow, so many things to eat. I’ll have bread._

\---

In the dictionary, if you looked up the words ‘good student’ and ‘quick learner’ you would find Dean Winchester’s picture. Castiel had already had suspicions about that being true, but never believed it until he woke up one morning in a hotel by the beach in Santa Monica to find Dean experimentally licking and sucking on Castiel’s cock.

 _That’s nice,_ Castiel thought, watching Dean’s movements carefully. It wasn’t the best blowjob ever—there was too much teeth and not enough spit—but for a first time, Dean was doing well. “How did you know,” Castiel finally said, “that one of my favorite things to wake up to is plump lips around my cock?”

The flash of crimson on Dean’s cheeks was exactly the reaction Castiel was going for when he spoke. In lieu of replying, Dean kept going, his mouth moving faster now that he knew Castiel was awake and paying attention. The effort it took to keep his hips planted on the bed instead of thrusting up into the wet cavern of Dean’s mouth, was a lot like trying to contain an atom bomb with plastic wrap.

And then, to prove the earlier theory that Dean really was the quickest fucking learner in the world, Castiel felt a lubed finger gently swirling around his hole. _Holy shit,_ the kid knew what he wanted and how to get it. “Mmm, please Dean.”

Dean’s finger was just about to push inside when a shrill noise sounded from the pile of clothes on the floor. In a flash, Dean froze and looked towards the ringing. They both knew who the ringtone was programed for in Castiel’s phone. The rapid change in Dean’s body language was obvious. Castiel watched him roll away and sighed as he slowly climbed out of bed and walked to the spot where his jeans lay. 

A picture of his wife and son flashed on the screen, bringing him back to reality. “Hello?”

“Daddy!”

His stomach twisted in a knot and Castiel balanced the phone between his ear and shoulder as he began to dress. “Hi Bo. Miss me?”

“Yes. When you be home?” Before Castiel could answer, Boston started in on a long description of what he had been doing for the last few days, his words flowing faster than Castiel ever had a chance of understanding. 

When he paused for breath, Castiel laughed. “I’ll be home soon, Bo. In time for lunch. You want to go somewhere special to eat?”

The boy squealed in delight. “Farm! I want to go to the Farm!”

Of course. Castiel should have known that answer before he even asked. A few blocks from their home was a farmer’s market with a locally owned restaurant called Farm to Fork—Boston was enamored with the place. He especially loved the kid’s corner where a small indoor playground was decorated like a stable.

“Sound’s like a plan, Bo. Just you and me? Or should we bring Dean and mommy along?”

“Mommy hasta work.” Castiel’s heart broke just a little when he heard the disappointment in his son’s voice. “Can we show Dean the Farm?” It was easy to hear the smile in his son’s voice when he spoke of Dean. 

“I bet he would love that.”

\---

Gabby wasn’t home when they arrived. Instead, they found Gabby’s assistant, Madeleine, on the floor playing with Boston and looking _way_ out of her element. When Castiel dismissed the woman, she practically ran from the house like the place was on fire.

After a quick change of clothes for Dean and Castiel, they gathered at the front door and Dean knelt down in front of Bo to help him put on his shoes. 

“So, Sir Boston,” Castiel said dramatically. “Stroller or walk?”

Boston looked to his left, staring into space as he brought a finger to his bottom lip and tapped it. “Hmm.” Dean glanced up long enough to catch the pondering look on Boston’s face and had to bite the inside of his cheek to keep from laughing. Bo finally looked back at his father. “Walk.”

It was a half mile trek to the farmer’s market and, not surprisingly, Boston was happily riding on his father’s shoulders after just a few blocks. Dean had made the suggestion, before they left the house, that they at least _bring_ the stroller, just in case… but _no_ , Sir Boston would hear nothing of such nonsense.

Thankfully, Farm to Fork was located at the entrance to the market so they were able to stop and eat lunch before doing anymore walking. 

While they waited for their food to arrive, Boston tugged on Dean’s hand until he followed to the kid’s play area. And despite many refusals and claims of _’I’m too big, Bo!’_ Dean rode on the back of a teeter totter that looked like a miniature cow.

After lunch, Boston was starting to look tired and like he was ready to go home and take a nap, but still demanded that they walk through the market and find something for dinner. 

Dean followed behind Castiel through the crowded aisles of food vendors. His boss held Boston tight in his arms so that the boy wouldn’t get lost in the maze of people. Dean could see the burden of holding the three-year-old was getting to Castiel. Even though Bo was small, he still got heavy if you carried him for too long.

“Here, why don’t I take him for a bit?” Dean said, holding out his hands to Boston. The boy turned to him and smiled happily, reaching for Dean as well.

After Castiel carefully placed Bo in Dean’s arms, he stared at them both for a few long moments. Dean couldn’t figure out what it was, but there was something sparkling in those calm blue eyes.

Castiel leaned forward, kissing his son’s cheek and smiling. Instead of straightening back up and continuing to walk, though, he focused his attention on Dean. The next thing Dean knew, Castiel’s soft lips were brushing gently over his as well.

The kiss was over as quickly as it began, and then Castiel was moving once more. Dean stood frozen, trying to figure out what had just happened. After a few moments he noticed Castiel walking away and rushed to catch up.

In spite of what had happened in the hotel room the night before, Dean had not really expected for things between them to escalate or change. He had fully assumed that life would go back to normal. Apparently he was wrong, because Castiel obviously felt comfortable enough to very blatantly kiss Dean. In public.

Not only that, but also in front of _Boston_. And though the boy seemed more interested in the shops than what his dad had just done, it didn’t mean that he hadn’t witnessed the kiss. Or that he wouldn’t later tell his mom without realizing that it might not be a good thing to share.

Castiel stopped in front of a fruit stand and, when Dean moved up next to him, leaned over to whisper in Dean’s ear, “I wish you could realize how gorgeous you are when you blush.”

Okay, _that_ was not helping! Dean turned to look at Castiel, feeling his cheeks flaming up again in a mixture of aggravation and embarrassment. “Do you really think you should be so obvious in public?” he hissed, looking around to see who could possibly be listening in.

“Yes.” Castiel leaned forward, kissing the side of Dean’s lips. “Because if you thought I was going to hide this, you’re wrong. I’m not ashamed of you, Dean.”

“Or, apparently, of the fact that you’re cheating on your marriage,” Dean spat. He shook his head, turning away from Castiel and continued on through the market. Boston’s head had laid down on his shoulder, and he knew that the boy must finally be falling asleep. 

After silently buying a few more things for dinner, they began the long walk back to the Novak home. They were a few blocks into the journey when Dean spoke up. “I know that you and Gabby have these… _rules_ or whatever, but that doesn’t mean I’m comfortable being flaunted as your other lover. For lack of a better term.”

Castiel sighed. “So no touching in public.”

“No touching at all.”

That caused the other man to stop walking and reach out a hand for Dean’s arm. When they were both standing in the middle of the sidewalk facing each other it was easy to see the frown on Castiel’s face. “I thought you enjoyed yesterday.”

“I did,” Dean replied, looking away nervously.

“But… you don’t want it to happen again.” 

It wasn’t a question, so Dean didn’t feel the need to answer. Instead, he laid a calm hand on Boston’s back and kept walking. He wasn’t going to risk his job just because having sex with his boss was really fucking hot.

Unfortunately, he wished that he could get the voice in the back of his head—the one that kept saying he was being stupid—to just shut the fuck up. He was making a grown-up decision for the good of everyone involved. 

And he was doing all he could to prevent another mishap with Gabby from happening.


	15. Chapter 15

_Toddler Tip: The moment when you realize adults don’t eat their vegetables either, they just instagram them._

\---

After eleven weeks of employment with the Novaks, Dean had established a routine. Controlling a three-year-old and avoiding tantrums meant having a well structured schedule in place—and making sure that it was always adhered to. This was wisdom from his mother and, considering she had been in the childcare business longer than Dean had been alive, he knew she spoke the truth.

On the wall beside the refrigerator was a six-foot tall chalkboard that the family used for writing notes and that Boston happily controlled the bottom three feet of. In one corner, written in blue chalk, was Dean’s schedule.

  * 7:00 am - Wake-up
  * 7:30 am - Breakfast
  * 8:00 am - Learning activities
  * 11:00 am - Gardening
  * 12:00 pm - Lunch
  * 12:30 pm - TV Time
  * 1:00 pm - Nap
  * 3:00 pm - Walk and/or play
  * 4:00 pm - Chores and clean-up
  * 5:00 pm - Dinner prep
  * 6:00 pm - Dinner
  * 7:00 pm - Playtime with mommy and daddy!
  * 8:00 pm - Bedtime (ONE story!)



Most days it was easy to keep on track, and Dean always allowed for thirty minute accommodations in any direction as long as bedtime and naptime were always on schedule.

The days when it didn’t work were when Castiel was working at home instead of in his office. The man lived for the opportunity to ruin all of Dean’s hard work; of this, Dean was certain. _No,_ time in front of the television couldn’t extend an hour into naptime. Of course there was absolutely _no way in hell_ that bedtime could be extended to ten p.m. so that Boston could stay up and watch a movie. And _yes,_ learning activities took precedence over playing hide and go seek.

More often than not, Dean was convinced that _he_ was Bo’s parent and Castiel and Gabby were just there to stir up excitement. But then again, it wasn’t really his place to speak up and complain—because he _wasn’t_ the parent.

“Damn it, Cas!” Dean growled under his breath. He knew he had to be quiet, because naptime had just started and it was laundry day—he needed the nap to last as long as possible to allow for all his chores to get finished. 

Of course, it would be a lot easier to do laundry if Castiel didn’t decide that it was a good time to make lunch and rearrange the _whole fucking pantry_. Dean stood in the small room that housed the washer and dryer and non-perishables and stared at the tornado disaster that had been left in Castiel’s wake. Whatever he had been after, had apparently required completely shifting two shelves into an unorganized mess. 

It wouldn’t be such a big deal if Dean hadn’t just spent the day before putting groceries away and coordinating the shelves into different meal plans for the week. 

Strong arms wrapped around Dean’s waist from behind and Castiel’s chin landed on his shoulder. “Did you call?” Castiel’s voice dropped to a more conspiratorial register. “Do you want a blowjob while Bo is asleep?”

He shoved the other man away and turned to glare at him as he pointed to the messy shelves. “What is this? I had that organized perfectly—it took me two hours! And now you’ve gone and shifted everything around. Why couldn’t you just eat what we had for lunch?”

“Because I can only handle tomato soup and space cheese once a month?” Castiel looked at the shelves before letting his eyes fall on Dean once more. “I’m afraid I don’t see the issue. It’s just a few cans out of place.”

“It’s a _system_ so that I know what to buy on the next shopping trip, and don’t have to spend precious kid-free kitchen time screwing around with what to make.”

Castiel nodded, reaching out to run his finger along a strip of colored paper that was stuck on one of the shelves. “I suppose that explains the color coding.”

“Days of the week are each assigned a color. I told you and Gabby about this _weeks_ ago, when I started it. Even Boston knows which color is for which day!” When Castiel opened his mouth to speak again, Dean shook his head and cut him off. “Forget it, I’ll fix it later.”

He brushed past his boss and ignored the softly spoken _’It’s just a shelf.’_ as he walked up the stairs to collect laundry. 

It had only been two days since Dean had put a stop to Castiel’s displays of affection—a helluva lotta good that did, considering the blowjob offer. To say that he was frustrated would be putting it mildly. It was bad enough that Gabby had been giving him the cold shoulder ever since Castiel had gotten back from New York.

As Dean picked up the laundry baskets and began the process of carrying them all downstairs, two at a time, the questions began to drift in his head once more. The most prominent, of course, was _had Cas told Gabby about the night in the hotel?_

\---

Gabby’s pregnancy hormones meant that at any given time she would get the urge to drag Castiel upstairs and have her way with him. Dean had reverted back to the way it was ten weeks before when he happily ignored every sound that came from their bedroom.

Once nine o’clock hit and Dean was certain that Boston wasn’t going to wake up again before morning, he quickly pulled his favorite hoodie on and headed downstairs and out the front door. He made sure his things were still tucked securely in his pocket and happily made his way to the small bench tucked beneath a tree in the Novak’s front yard.

When he needed an escape, he hid there. He could always get in his car and go somewhere—even walk down the street to the park—but he was never confident enough to leave like that without Castiel and Gabby knowing to listen for Boston. It was ridiculous how attached to the kid he had grown in less than three months. With Gabby hitting the six month mark in her pregnancy, he couldn’t help but wonder how things would change when the new baby arrived. Dean had at least three arguments a day with Bo about whether or not it’d be a boy or a girl. Unfortunately, Gabby wanted it to be a surprise.

Once Dean was mostly secluded in his favorite spot, he pulled a lighter and a pack of Camels from his sweatshirt pocket. He wasn’t a big smoker—hell, one pack had lasted him almost a month at that point—but after a particularly stressful day, he needed it. He needed some way of zoning out and forgetting about his employers having sex. 

His head was tipped back and his eyes closed as he blew smoke up into the night sky—when a body sat heavily onto the bench next to him.

Dean startled immediately, looking at the other person in shock. He expected it to be Castiel, following him out and probably ready to come onto him again. 

It was _not_ Castiel.

On the other side of the bench sat a 20-something _hipster_ wearing black framed glasses and a beanie pulled down over wavy hair and too-long sideburns. Dean stared, rendered speechless at the surprise appearance. In the hint of moonlight he could make out sparkling golden eyes and— _was that a soul patch?_ Did people still do that?

Definitely a hipster. “Can I help you?” he finally managed. The guy was smirking at Dean like he belonged there, despite the fact that Dean was ninety-nine percent sure he _didn’t._

Hipster dude smiled, showing off the faintest of dimples. “Can I bum a smoke?”

Dean looked around the yard, feeling like he was being punked or something. “Excuse me?”

Not waiting for an answer, the guy leaned into Dean’s personal space and grabbed the forgotten cigarette from his hand. He took a drag off of it, still smiling. When he finally let out a puff of smoke into the night air, he flicked his golden gaze back to Dean. “Billy McKenna. Nice to meet you. I take it you’re Dean? The new wet nurse?”

It took a ridiculous amount of time for Dean’s brain to catch up. Now that he wasn’t worrying over the fact that a perfect stranger had sat down and stolen his smoke, he could see through the moonlight and realize that he had seen the hipster’s face before. Over the mantel in the Novak home. “You’re Gabby’s brother.”

“The one and only, hot stuff.”

Dean watched Billy continue to smoke _his_ cigarette. “You’re supposed to be in fucking Peru or some shit.”

Billy snorted, passing the cigarette back to Dean now that it was almost gone. “Also known as: grad school in Seattle.”

“But Cas said—”

“Ah, yes, my amazing brother-in-law Castiel.” Golden eyes shifted to the two-story house behind them. “Banging my sister right about now, I’m guessing. At least based on the fact that you’re out _here_ instead of in _there._ ” Billy looked to Dean again and shrugged. “I’m not high on Castiel’s list of favorite people. Last time I was here, I put hair dye in his shampoo and he walked around with purple hair for a week.”

Dean had seen that picture when cleaning. It was hilarious. “And you’re here now, because... ?”

“Spring break, Deano. I came to see my big sister and nephew and to enjoy a week with the hot guys of Los Angeles.” Billy leaned closer, once more crowding into Dean’s personal space. “So… got any plans, hottie?”

**Notes for the Chapter:**

> If you can't figure out the actor who plays Billy - _what's wrong with you?_ There are only SO MANY hints that an author can give!


	16. Chapter 16

**Notes for the Chapter:**

> Yes, Billy is played by the wondrous Speight. If you haven't heard him sing on Jason Manns' new album - whats wrong with you?!

_Toddler Tip: Anyway for breakfast I'll have 6 plain pancakes with a circumference of no more than five inches but no less than six._

\---

A few minutes after the surprise introduction and overly-flirtatious conversation in the front yard, Billy followed Dean into the house. He picked up a large duffel bag sitting on the front porch that was big enough to suggest that maybe a ‘week’ wasn’t seven days in Billy-speak.

In the light of the living room, Dean was finally able to see Billy clearly and if he had thought the sideburns and soul patch were interesting style choices they were nothing compared to the rest of Billy’s ensemble. The guy was wearing skin tight, bright fucking _purple_ jeans. He took off a baggy grey sweater with a wolf on it to reveal a short-sleeved plaid button up that was tucked into his pants and buttoned all the way to his neck. And, to complete the outfit, yellow and green striped suspenders and a black bowtie.

The whole thing was just ridiculous. Dean wasn’t ashamed to admit that he stared for a good minute at Billy’s apparel as Billy dropped his bag and kicked off a worn-out pair of Converse.

“Are you wearing a bowtie?” Dean finally asked. To be fair, the plain black bowtie was actually the most _normal_ aspect of the outfit.

Billy shrugged, turning to look around the house. “Bowties are cool.”

There were noises and voices coming from the kitchen, so Dean followed Billy in that direction after making sure the front door was securely locked. Although, he wasn’t quite sure what good it would do since he had already let crazy walk right into the house.

In the kitchen, Gabby and Castiel were making snacks and Gabby raised her head up at the sound of footsteps. Noticing her brother, she gasped. “Billy!” She moved to him in a rush and wrapped her arms around him in a tight hug. “What are you doing here? You said you were going on an ‘excursion’ for you break.”

While Billy explained his reason for coming to see his sister and her family, Dean stood back and watched the emotions playing out on Castiel’s face. Despite Billy brushing off Castiel’s dislike as mostly harmless, Dean got the feeling that there was more to the story. He had never seen Castiel look so uncomfortable.

Billy said a few words down to Gabby’s swollen belly before looking across the kitchen and smirking at the sight of his brother-in-law. He wrapped a casual arm around Gabby’s shoulders and addressed Castiel. “Hey, snoodle bear, what’s happening?”

Castiel scoffed and forced a smile. “Billy. Nice to have you back for another surprise visit. How long can we be expecting you for this time?”

“Oh, I don’t know.” Billy grinned, running his free hand over Gabby’s belly. “When’s the baby due? Three months?”

A silent rage seemed to be brewing under Castiel’s skin, and Dean had to fight back a laugh as he watched his boss hide the emotion with a plastered-on smile. It was equal parts hilarious and interesting to watch Castiel’s reactions.

Gabby moved away from her brother and back to the counter where her snack was half prepared. “I’m glad you’re here, little brother, but now that Dean is living here full-time, and the spare room has been converted to a nursery we don’t have anywhere for you to stay. I’d offer you the couch, but I know how much you hate that.”

Billy pulled out one of the barstools that sat against the kitchen island, and perched on the edge of it. His eyes swept from Gabby, to where Dean still stood at the edge of the kitchen. “No worries, Bree. Dean and I were talking outside. We already agreed that it wasn’t a big deal if we just shared his bed.”

The jar of peanut butter that Castiel had been putting away landed on the floor with a loud thud. Ignoring it, Castiel stared at Dean. “You _what_?”

Dean was as shocked as Castiel but, when he looked to Billy, he saw a knowing smirk on the man’s face and pushed back any argument. There was no way he was going to share his bed with Billy, but he could have that conversation later and still enjoy the panic and jealousy flashing in Castiel’s eyes. So he shrugged his shoulders and finally replied, “It’s cool with me.”

At that point, it became very obvious where Boston had learned to pout. Castiel picked up the peanut butter jar and set it on the counter, before grabbing his sandwich and storming out of the kitchen with a forced, “Goodnight.”

Gabby watched her husband go and frowned before picking up her own sandwich and brushing off Castiel’s behavior with a laugh. “He’s just pouty because I made him wait to come. You boys behave. Billy, I’m glad you decided to come for a visit. I’ll see you in the morning.” She kissed her brother on the cheek and followed Castiel’s path up the stairs. 

Left alone with Billy once more, Dean nervously peered down at his hands. He really needed to trim his fingernails.

“Oh man, I can’t wait to take a shower. The water pressure in my apartment is shit.” Billy stood, brushing past Dean and moving back to the foyer to grab his duffel bag.

When Dean heard him going towards the stairs, he was finally jolted into movement. He quickly followed. “Wait—you weren’t serious, were you? You can’t sleep in my bed!” 

“Of course I can, Deano. You just said a few minutes ago that it was fine with you if I did.” Once upstairs, Billy walked down the hallway and straight towards the closed bedroom door that was Dean’s. Before he opened the door, he turned back to Dean for a moment and winked. 

Apparently calling Billy’s bluff so that Dean could enjoy seeing Castiel look jealous had been a major mistake. Now he was stuck sharing a bed with Billy for who-knew-how-long because if he backed out and went to sleep on the couch, the effect would be lost. Not to mention, he really didn’t want to sleep on a sofa for a week or more.

Dean slowly stepped into the bedroom, making sure to close the door quietly so that nothing woke Boston up. He really didn’t want to deal with a cranky three-year-old on top of everything else.

Billy had carried his bag to the chair in the corner of the room and was carelessly rifling through it, not worried at all about the clothes that went flying over his shoulder. “So how long have you been sleeping with Cassie?”

It was going to take a ridiculous amount of time to get used to Billy’s bluntness. Dean’s first instinct was to lie, but that’s what Billy would be expecting and _two_ could play the game of shock and awe. “Half a week. Well, I don’t suppose that really counts. We slept together once, half a week ago.”

“Was he good?” Billy asked, unphased by Dean’s honesty. He stepped away from the chair with a pair of sparkling pink boxers and a bottle of shampoo. When he looked to Dean, his eyebrows were raised in question.

 _Too good,_ Dean realized. “Yeah.”

“Always figured he would be.” He carried his things into the bathroom, but left the door wide open. 

A few seconds later, Dean could hear the water start to run and, from the angle he was standing at, could see Billy’s backside as he stripped. The man obviously had no shame.

Shaking away his thoughts, he moved to his dresser and opened up the drawer that held his sweatpants and basic t-shirts. He picked out a pair that would be comfortable to sleep in and carried them over to the bed with the intention of changing before Billy finished his shower.

Before he could get to that point, though, Billy spoke from the bathroom doorway. “Hey, it’s been a while—I don’t remember how to make this damn faucet switch over to shower mode.”

“Oh it’s—” Dean turned, ready to toss out the easy instructions. He was not expecting to see Billy standing stark naked in the glow of the bathroom light. His mouth and brain simultaneously stuttered as he stared at the expanse of pale skin before him.

The fact that Billy looked completely different in comparison to Castiel was not lost on Dean. Where Castiel was older and experienced, Billy had a definite ‘young and wild’ vibe; instead of Castiel’s short dark brown hair, Billy had long blonde locks that brushed along the back of his neck.

And, instead of coarse brown hair at the base of his cock, Billy was completely shaven and… _fuck_ why was that hot?

Hands on his hips, Billy continued to stare at Dean with a smirk on his face. “It’s…?” When Dean didn’t respond, Billy offered another solution. “Maybe you should show me.”

Dean’s feet felt like they were attached to buckets of concrete, but he managed to slowly make his way across the floor. When he reached the doorway, though, Billy remained standing there— blocking his path. “Uhmm… ”

“I never thought I’d be jealous of my brother-in-law, but the fact that he’s got a thing going with such a hot virgin is really making me see green.”

“What?” Dean shook his head. “We aren’t a thing. And I’m not a fucking _virgin_.”

“No?” Billy stepped forward, pressing into Dean’s personal space with every movement. When he was finally settled completely against Dean’s chest, looking up the few inches of height difference to see Dean’s eyes, he spoke. “Not a virgin, huh? So just how many cocks have you had in this pretty... little... tight…” His next word was punctuated by his hands reaching around and grabbing Dean’s butt. “ _Ass_?”

Dean grunted, wanting to deny the fact that Billy was turning him on, but it was pretty much impossible with his body pressed so close to Dean’s. There was no way Billy couldn’t make out Dean’s erection through his jeans. He stuttered, trying to make his brain work as he stared into golden eyes. “I don’t bottom.”

“Well, I hate to break it to you, Deano, but you’re missing out on the best part.” Billy’s hands were still gripping his ass and slowly started a makeshift massage of Dean’s buttcheeks. “If Cas hasn’t told you the joys of having a thick cock sliding along your prostate, then he’s obviously keeping all of the good stuff for himself.”

Dean shivered, remembering the way Castiel had reacted to Dean stimulating his prostate. But still, the thought of being so submissive, reminded him of Gabby’s continuous torture and there was no way he was going through a process like that again. “I just…”

In a flash, Billy pulled back and stepped farther into the bathroom. “Your loss. Now—why don’t you show me how to turn this shower on, and I’ll repay you with a blowjob?”

Unlike Castiel’s earlier offer, Dean wasn’t sure he could turn this one down.

**Notes for the Chapter:**

> Did anyone catch the Doctor Who reference? ;)


	17. Chapter 17

**Notes for the Chapter:**

> *mumbles about spoiled readers*

_Toddler Tip: I'll be in the family room sitting in your lap while you also cook in the kitchen. Love you. (so hungry)_

\---

If one thing was for certain, it was how much absolute love Billy and Boston had for each other. When Bo woke up Thursday morning to the sight of his uncle sitting at the breakfast table he _screamed_ in utter delight.

Dean watched all of this unfold from his spot making breakfast in the kitchen, and couldn’t hold back his smile. Usually it took a couple hours to get Bo up and ready to go, but he was already bouncing around and asking his uncle a million questions. Once he was settled enough, and Billy informed him that there would be no ‘fun time’ without breakfast, they all sat down to eat the pancakes that Dean put on the table. 

Dean had to admit he wasn’t that surprised when he had stepped out of his bedroom and Castiel and Gabby were both already gone for the day. He had a feeling that Castiel was still more than a little pissed about the night before. Of course, in the light of day, Dean wasn’t sure that he should have gone so far and made such an effort to make his boss jealous—especially not when he was _trying_ to step back and ignore his feelings.

He was in a place that he definitely didn’t like being in—but that didn’t make Billy any less fun to be around. Even sharing a bed with the guy had been an experience. Who knew that one little dude could commandeer so much of a queen-sized bed?

\---

“I can’t believe I let you talk me into this.”

Billy scoffed. “It’s Thursday—the place will be dead.”

“It’s the largest tourist attraction in California. I don’t care what day it is—it’s going to be _packed._ ” 

“Yeah, but the kid’s happy.”

As he continued walking, Dean looked over the top of the stroller that he was pushing and smiled when he saw the excitement on Boston’s face. The kid was _definitely_ happy. 

—Until one o’clock came around and he started to get cranky because he wasn’t at home on his usual nap routine. But they were already standing at the gates of hell… er, _Disneyland_ , and there was no turning back. 

Dean watched Billy pay for their tickets and then pushed the stroller through the gates, stopping for security to check the backpack he had brought, stuffed with food, water, and an extra change of toddler clothes. Billy himself seemed to have toned down the fashion today. His corduroy pants were a modest mustard yellow, and slim-fitting. His t-shirt was looser, purple, and had an equally purple dog on it. His not-quite-shoulder-length hair was swept up in a messy knot at the back of his head (“It’s a called a _man-bun_ and it’s very practical, thank you very much”) that would have made Dean roll his eyes had he seen it on anyone else but, on Billy, it worked.

Once they were past security, Billy leaned down to Boston’s level and addressed his nephew. “Where to first, squirt?”

\---

After five hours, three trips on _It’s a Small World_ , and one puke accident that required a wardrobe change Dean was ready to walk away from Disneyland and never look back. He carried Boston in his arms, because the kid wouldn’t stay asleep if he was put back in the stroller (and cried at even the _mention_ of his uncle carrying him), and followed Billy back towards the park gates. Dean was exhausted, to say the least, but the pictures tucked in his backpack of Bo shyly kissing Belle made it all worth it.

“I can’t believe how much the kid loves you,” Billy observed, pushing the stroller through the exit gate a few steps ahead of Dean. “I think he might love you more than his mom.”

“Yeah, right. I’m the mommy replacement—he loves me until Cas and Gabby are in the room. Then he ignores me, for the most part.” Dean frowned. “I wish they spent more time with him. I think he has developed talents that they aren’t even aware of. Like, on Tuesdays he helps me cook each meal, and he’s figuring out spice combinations faster than I ever could have imagined. Sometimes I forget that he’s only three.”

“Right.” Billy laughed. “It seems that the love goes both ways.”

They made it back to the car and while Billy struggled to fold up the stroller and store it in the trunk with all of their souvenirs, Dean swiftly buckled Boston into his carseat before the boy woke. He set his backpack in the seat next to Bo, and climbed into the passenger side. The only thing waiting for them was _lots_ of traffic and, “Damn it. Rush hour.”

Fifteen minutes later, they were stuck on the freeway and moving nowhere fast. To pass the time, they shared stories about their childhoods and Dean felt a pang of sadness at the thought of his mom and brother. He missed them… a lot.

They were halfway home when Billy finally broached the topic of Gabby, Castiel, and sex. “So, I know about what happened between you and Cassie—but I’m curious, have you slept with my sister as well?”

Dean was taking a drink from their last bottle of water and almost did a spit take at Billy’s question. “I, uh… excuse me?”

“Don’t play dumb, Deano. I know about my sister’s so-called ‘poly’ lifestyle.” Billy rolled his eyes, his fingers tapping sporadically against the steering wheel. “You know all of that is bullshit, right? I love Bree to death, but when she told me that her and Cas had an open marriage, I knew it was nothing but an excuse.”

Billy’s words had him confused. The guy seemed way too liberal to be against something as trivial as polyamorous relationships. But it seemed like there was more to the story. “You don’t approve of open marriages?”

“I don’t approve of my sister being in one.” Billy shook his head. “You know what Gabrielle was like before she got married?” When Dean replied that he had no idea, Billy continued. “Her longest relationship was _maybe_ three months. There was a new guy every week, and sometimes more than two guys at a time. She moved here and went hog-wild with the whole ‘I’m a celebrity’ bit, and slept with everyone she could get her hands on. When she got married, I told myself there was no way it would last. But she got around the commitment issue by convincing Cas to agree with the ‘open marriage’ concept. Now she can sleep with whomever she wants, and still have a family.”

Dean would have liked to say that he was surprised, but he wasn’t at all. His feelings towards Gabby had already soured after the way she treated him two weeks before, and what Billy was saying was doing nothing but making it worse. Because, his thoughts immediately turned to Castiel and Boston. Hell, even the new baby. They were all pawns in creating Gabby’s perfect world, and Dean wondered if she really loved any of them. 

For all he knew, she had a family to keep up appearances in Hollywood. 

Castiel and Bo deserved so much better than that. But, unfortunately, there wasn’t much that Dean could do. He was just the fucking nanny.

\---

After they got back to the house, Billy helped Dean unload everything before heading out again to go meet up with old friends. Boston was awake, but definitely still worn out, so Dean set him up on the couch with a movie before going into the kitchen to make dinner.

He was in the midst of putting together a vegetable and pasta dish when he heard Castiel arrive home. The usual cries of excitement from Bo were much softer than normal and, after a few minutes, Castiel stepped into the kitchen with his eyebrows raised. “Hey. I take it you two had a busy day? You look as exhausted as Bo does.”

Dean nodded, opening the spice cupboard and pulling out a variety of seasonings. “Billy thought it’d be a good idea to go to Disneyland.”

“Ouch,” Castiel replied, his voice laced with an edge of sympathy. “We’ve only done that once before, and it was horrific. Did you have a little bit of fun, at least?”

“Right up until Boston got sick on the Teacups, yes.” He left the pasta to simmer and moved to set the table. Since Billy had said he would be out late, Dean automatically pulled out two regular plates and one of Bo’s space plates. He paused though, fingers on the edge of a third plate. “Is Gabby going to make it for dinner?”

“No. She left for a two-day shoot in Dallas.” Castiel pulled the plates from Dean’s hands and took over the task. “Listen, Dean…” He laid out the dishes and looked across the room to meet Dean’s gaze. “I want to apologize for my actions the last couple of days.” Once the table was ready, Castiel moved back into the kitchen, closer to Dean—but not close enough to cause issue. “I don’t want you to think that I was trying to force you into anything.”

“I don’t—”

Holding a hand up, Castiel cut him off as he stepped closer. “Dean, I like you… a lot more than I should. I like the person you are when you’re in your element, organizing our lives and taking care of Boston like he’s your own son. But I also like the person you are behind closed doors; the one that you don’t let many people see because you’re afraid of looking weak or vulnerable.” Dean’s breath caught in his throat and dinner was long forgotten as Castiel closed the distance and pressed up against him. His forefinger and thumb gripped Dean’s chin, keeping Dean still and their eyes locked. “I like every part of you, and when you said that you didn’t want anything to happen between us again… it killed me.”

Gently, Castiel leaned forward to kiss Dean’s bottom lip. Dean’s eyes slipped closed and he barely found the effort to whisper, “ _Cas._ ”

“I can’t promise you anything, Dean. And I have absolutely no claim over you or your actions.” Another gentle kiss, this time to the corner of Dean’s lips. “But please… I’m _begging you_... don’t sleep with Billy.”

Dean had no answer to that, but Castiel obviously wasn’t expecting one when he cut off all chances of a reply with a kiss that had Dean seeing stars.


	18. Chapter 18

**Notes for the Chapter:**

> OKAY... so, three updates in three days means you guys are obviously well spoiled, and now it's time for me to break your hearts. I have to finish my Team Free Will Big Bang story before the 20th, so Tiny Vessels will NOT get an update before Saturday. (Believe me, the muse is pouting as much as you are!) 
> 
> As payment for your suffering (because five days OH MAN) - I promise that Chapter 19 WILL answer TV's most important question: _Did Billy blow Dean or not?_

_Toddler Tip: She signed me up for some kind of toddler crossfit. I know I have a belly but this is wrong._

\---

_’Being in a ‘love triangle’ is not all it’s cracked up to be.’_

Dean felt a frown creasing his eyebrows at _that_ particular wording. He was not in a God damn love triangle! He stared at his phone for another minute, before typing out a reply. _’Not. A. Love. Triangle.’_

It took only moments for Sam’s reply to pop up on his phone. _’Dean, you have two people fighting for your attention. Definition of a love triangle.’_

He pouted, not wanting to admit that Sam might be right. From his spot on the back porch, he looked up and tracked Boston’s movements, making sure the boy was still okay as he played. Sometimes Bo wanted to play in the garden without supervision, so Dean had to keep a close eye on him in protection of all their combined hard work. 

Boston was still happily playing with a couple of Tonka trucks in the grass, though, so Dean let him be and went back to his phone. _’Shoulda known bettr than 2 ask 15 yo for advice’_

A reply text didn’t come through. Instead the phone began to buzz and Sam’s face popped up on the screen with an incoming call. Dean answered, rolling his eyes at the same time. “Too good for texting, punk?”

“I find your lack of proper English and grammar to be disturbing,” Sam replied. “Since mom isn’t home, I figured I could just call and get the truth from you. I know there’s more to the story than what you’re telling me. How are you even meeting chicks? I thought you were on nanny duty 24/7. You aren’t using Boston to pick up girls, are you?”

“No.” It was crazy to think that _that_ would have been the drama free alternative. Dean glanced around once more, making sure that Billy was still gone and Castiel hadn’t snuck home early from work. Once he was positive there were still no other adults around, he took a deep breath. “So, listen, I’m not happy about talking to my kid brother about this bologna—” Sam snorted at Dean’s avoidance of a cuss word; Dean happily ignored him. “But I have no other options, so keep all opinions to yourself until the end of the ride, _please._ ”

Once Sam agreed… Dean told him everything. Not just the ‘hey, your older brother might be a little gay’, or the ‘so I spent a week as my boss’ sex slave’ parts. _Everything._ Fifteen minutes later, Sam was still quiet on the other end of the phone and Dean ended his retelling with a soft, “I don’t know what to do, Sammy.”

“Fuck, Dean,” Sam said. It was his only reply for a few beats, as he seemed to be composing his thoughts. The great thing about Sam was he had inherited the best of their parents’ personality traits, which meant he was always straightforward like their father—but compassionate and loving like their mother. “You know, I haven’t even met the woman and I don’t like Gabby.”

Dean snorted, because of _everything_ Dean had said—that was the part Sam was focused on. “I can’t say I’m the biggest fan either. But it’s moving away from being upset about how I was treated, and onto worrying about how she treats Cas and Bo.”

“Well then, that’s a big hint.”

“It is? Enlighten me, Mr. Smarty Pants.”

Sam sighed, and Dean could practically feel the kid rolling his eyes over the phone. “You’re worried about Cas and Bo, which means that intense feelings have been established for them. If you take this Billy character out of the equation—because honestly, he’s just causing problems—the focus has to be on _why_ you pushed Cas away.”

Which was exactly why he was focusing on Billy in the first place; so that he could ignore his feelings for Cas. “For damn good reason,” Dean argued. “Because he’s married. He has a family. I’m just the freakin’ nanny.”

“Wouldn’t be the first time that a guy left his marriage for a nanny.” 

“No. I’m not doing that to Bo. The kid deserves to have both of his parents together. This is exactly why I told Cas to back off. I can’t—” Dean ran out of words as he felt the emotions gang up on him. He brushed a shaky hand down through his hair and over his face. Three months. Three months was all the time it took for him to fall so deeply in love with Boston that he would sacrifice his own happiness for the kid. “I can’t, Sam.”

“Fair enough.” Sam remained quiet for a moment, giving Dean a chance to gain control once more. When Dean’s breathing evened out, Sam continued. “I think it’s obvious that you aren’t cut out for this whole open marriage concept. If I were to give one piece of advice, it’d be to stop that all together. Stop dipping your toe into murky waters. Don’t just tell Castiel off—establish ground rules in regards to what is and isn’t appropriate. And don’t use Billy as a means for making Cas jealous, because that’s just taking another step backwards.”

“So basically—keep it in my pants.”

Sam snorted on the other end of the phone. “I know it seems like an impossible task, but I have faith in you.”

\---

Setting ground rules with Castiel was easier said than done. Mainly because it was hard for Dean to pretend he was emotionless as he sat across from Cas and explained that they really couldn’t keep on as they had been. Castiel put on a good show of accepting the rules, but Dean could still sense the underlying heartache.

It made the rest of the night unbearable, for the most part, and Dean was actually relieved when Gabby got home and stole Castiel’s attention away once more.

Saturday morning, when Billy asked Dean if he wanted to tag along and spend his day off at the beach with Billy’s friends, he happily accepted the excuse to get out of the Novak house. Once at the beach, Dean was introduced to a group of three guys and two girls and convinced to take impromptu surfing lessons from Billy’s friend Raymond. 

Even though they weren’t the type of people he would normally hang out with—because really, who knew California beach bums were really a _thing_ —Dean had a blast. He wiped out on the surfboard more times than he could count, but always came back up from beneath the water with a wide smile on his face. 

When the sun began to dip towards the horizon, someone pulled out a few wine coolers. The group built a bonfire and sat around it in a circle roasting tofu dogs and marshmallows (Dean sampled _one_ tofu dog before deciding marshmallows and Doritos were a sustainable dinner). Dean took up the spot between Billy and a blonde named Rhonda and happily sang along when someone broke out a guitar.

After the sunset, a joint was lit up and passed around, and when Rhonda held it out to him with a twinkle in her eye he knew that he was not going to survive the night sober. He took a long drag before passing it to Billy. “I hope you have an alternative plan to driving home tonight,” Dean mused. He could see a large case of beer being dragged into the circle and knew that an argument about his not-yet-legal age wasn’t going to stop them from getting him to drink.

“Don’t worry, babe. Rhonda has the sweetest little set up a couple blocks from here. She lets everyone crash at her place after parties.”

Dean glanced back to Rhonda and watched her wink.

Nope, he wasn’t going to survive.

\---

The next morning, Dean woke up with a pounding headache and not even the faintest idea where he was. He could feel bodies pressed up against both of his sides—which was confusing enough to make the headache _worse_ —and when he wiggled around, it felt like he was laying on fucking concrete. Everything hurt. His back, his head… his ass. He groaned, trying to move away from the people tangled against him so that he could slowly sit up.

When he tried to move, a hand pressed against his chest to keep him in place, and he heard Billy mumble in his ear, “Ten more minutes.”

It sounded like a good plan, until his bladder reminded him of what had woken him in the first place. “I gotta piss.”

Billy grumbled a response and rolled away, allowing Dean to pull himself up. It took more than a few seconds for his brain to register where he was. A nice wooden _floor_. That explained the back pain. He looked around the floor, seeing Billy laying on one side, clad in only orange and green checkered print briefs, and Rhonda on the other. Dean couldn’t help but notice she had somehow fallen asleep in nothing but a teeny, tiny thong—leaving her breasts in plain view. When he turned to look behind him, he frowned with the realization that his pillow had apparently been some guy’s stomach—one of the other partygoers that he couldn’t remember the name of. He was dressed down to his skivvies—a tasteful pair of green plaid boxers, thankfully—as well. 

Well, then.

He pushed himself to his feet, completely unaware of where the bathroom was, but intent on finding it. Thankfully, the first door he happened upon was open and was indeed the room he was looking for. He stepped inside, shut the door behind him and flicked on the light. _Bad idea._ The bright luminescence had him squinting his eyes shut immediately while his head throbbed in protest. _Ow._

Dean waited patiently for a minute before blinking his eyes back open and moving to the toilet. When he reached down to pull his dick out of his boxers, his hand stopped midair and he stared in shock. Instead of the blue boxers he had on earlier, he was now wearing a pair of bright pink satin panties with white lace trimming the top. 

_Holy shit._ What the _fuck_ had happened last night?


	19. Chapter 19

**Notes for the Chapter:**

> All complaints and tomatoes can be sent [here.](http://hufflecas.tumblr.com/ask)

_Toddler Tip: I get that last night was a nightmare but why she have to dress me like 2T Freddy Krueger?_

\---

Throughout breakfast—which was way too greasy for his hangover—Dean got bits and pieces of the story from the night before. The problem was no one seemed to remember every event clearly. From the sounds of it, they had had a pseudo orgy before they all passed out. Someone could clearly remember that Dean and Billy had made out, before Dean had moved onto making out with Rhonda.

And at some point, according to Billy, Dean had licked his way down Rhonda’s body and, “Practically split her open on your tongue. It was fucking hot.”

Rhonda smiled at the reminder, but didn’t offer up a definite opinion on whether or not it had really happened. She merely motioned to Billy with her fork and continued the retelling. “And since Billy thought it was so hot, he figured you deserved a reward for your efforts. So he asked if you had ever been rimmed before, and then he fucked your ass with his tongue and fingers. I didn’t see that part, but I felt you yelling about how good it was against my pussy.”

“Bull _shit_ ,” Dean said, looking back and forth between the two, before glancing at the other three people in the room. Everyone nodded their heads in agreement. Well then. His eyes moved back to Billy. “Thanks for not fucking me while I was inebriated.”

Billy winked, looking ridiculously put together for someone that was hungover as hell and wearing yesterday’s clothes. “No problem, doll.”

While Billy and Rhonda cleaned up after breakfast, Dean went on a hunt through the odd array of clothes until he found his board shorts and t-shirt from the day before. It occurred to him, as he pulled the shorts on, that he was still wearing the silk panties. In fact… he had sat through all of breakfast wearing nothing but the panties. No one had said a word and he was way too hungover to care. But… since they weren’t exactly _un_ comfortable, he left them on beneath his shorts and pulled on his shirt. 

Once he was dressed, he slipped his phone from his pocket and noticed that the battery had died at some point during the night. “Hey Rhonda,” he called, holding his phone in the air, “didn’t I see you with the same phone last night? Can I borrow your charger?”

“Sure. It’s plugged in over by the couch.”

“Thanks.” 

It took a few minutes for his phone to turn on once it gained some battery life, but when it did—the device went nuts. He immediately had fifteen new text messages and six missed calls, as well as a lone voicemail. That wouldn’t make his heart race so much, if they weren’t all from the same number.

_Castiel._

Dean checked the latest of the text messages. _’Where are you, Dean? Bo needs you… I need you.’_

His stomach sank and he flicked back to the voicemail to listen to what it said. According to the log, the message was left at 11:48 p.m., the night before.

_”Dean? God damn it, Dean, why aren’t you answering? We’re in the ER at Cedars Sinai—Boston got into something in the bathroom.”_ Dean felt like he was going to throw up as he heard the fear and panic in Castiel’s voice. _”Fuck, Dean, I’m so scared. He just started getting so sick… where are you? Why aren’t you answering? Please, Dean.”_

The message cut off and Dean quickly unplugged his phone and stood, rushing to find his shoes as he called out for Billy. “Billy, where the fuck is your phone? Why didn’t you hear it?”

Billy peered around the corner and stared at Dean in confusion. “I left it in the car, remember? I didn’t want to lose it on the beach.”

“Well get your shit, we have to go. Bo ate, or swallowed, something and got sick. I had a bunch of messages from Cas—they’re at the hospital.”

\---

Billy tried calling Castiel and Gabby from the car, but couldn’t get a response from either of them, so they drove straight to the hospital, figuring they could get in touch with the two once they were there. It was a good thought that was quickly struck dead as soon as they walked up to a nurse’s station and asked for directions to Boston Novak’s room.

“I’m sorry but I’m not allowed to give out personal patient information,” the woman answered automatically. 

Dean glanced around, feeling his anger boiling—fed by the fear that he felt in his heart. It took him a moment to realize why the woman would be screening visitors. He slapped Billy’s side. “It’s L.A., they think we’re reporters.” Dean turned back to the woman and shook his head, “I’m Boston’s nanny, and this is his uncle Billy McKenna. Just call up to his parents and I swear they will confirm who we are.”

She tore her gaze from Dean and looked to Billy. “Do you have identification, proving you’re Billy McKenna?” With a nod and shaky fingers, Billy pulled out his wallet and showed the woman his driver’s license. Dean was about to do the same, but wasn’t given the chance before the woman spoke up again. “I have approval for Mr. McKenna to be allowed upstairs.” She gave Dean a sympathetic smile. “I’m sorry, that’s the only person I can allow—the only information I have here in my system. If you want, you can have a seat over there in the waiting room and I’m sure Mr. McKenna can deliver the message that you’re here. Once the family approves it, I can allow you upstairs.”

Dean felt sick as he stumbled away from the desk. Sure, he wasn’t family, but they had called for him to be there. They obviously wanted him around, so why wasn’t he approved to see Bo? Or hell, to even get information on whether he was alive or… _fuck._

“Dean?” Billy gripped his arm to focus Dean’s attention. “Just have a seat and I promise I’ll have them call down and fix this as soon as I get up there. Hell, you deserve to be up there more than I do.”

“Yeah.” Dean nodded, waving Billy away. “Go. Just go. God… just make sure he’s okay.”

Billy hesitated another moment, before finally turning to follow the security guard that had arrived to escort him upstairs.

Dean crumbled into one of the plastic waiting room chairs, making sure to find a spot near a power outlet so he could charge his phone with the cord Rhonda had let him borrow. He tried Castiel’s number once more, hoping on a whim that he would pick up, but it went straight to voicemail. He left a message, his voice broken. “I’m here. I’m downstairs. I’m sorry I wasn’t there last night. Please… they won’t let me upstairs, Cas.”

In the virtual void of a hospital waiting room, time seemed to pace both quickly and slowly. Without the patience for anything else, all Dean could do was shift his gaze between the clock on the wall and the hallway that Billy had disappeared down.

Five minutes turned to ten turned to thirty turned to an hour and with each second that past, Dean felt a little worse. Finally, after seventy-five long minutes, Dean heard his name being called from across the room. 

“Dean Winchester?”

He looked up, spotting a short man in a suit standing there looking around expectantly. Dean pocketed the phone and charger and stood. “That’s me.” He moved forward on shaky legs, trying to gauge whether the man was a doctor or another member of security. Neither role seemed to fit.

The man was holding a large manila envelope, and when Dean stepped up to him, he shifted the envelope to his left hand, and held out his right to shake Dean’s. Something in Dean’s head screamed _too formal… not right_ and he got a sinking feeling in his gut.

“My name is Charles Donahue, I’m the personal attorney for Mr. and Mrs. Novak. They’ve asked me to deliver this to you.” Charles Donahue placed the envelope in Dean’s hands and waited patiently. 

Dean bit his bottom lip, hesitating a moment before opening the large folder. Inside was a single sheet of paper and a check made out to Dean. He barely glanced at the check as he stared at the paper, too shocked to comprehend the words that he was reading.

In large bold letters along the top of the paper, it read clearly: **Letter of Termination**.

“What?” he gasped, unable to understand what was happening. His vision was starting to get blurry as he looked back to the man. “What the fuck is this?”

“The Novak’s are no longer in need of your services. The check included is equal to three months, as a stipend for the sudden termination. A security professional is waiting by the door to drive you back to the Novak home, where you are to pack your things and leave the premises by the end of the day.”

He felt like he’d been sucker punched in the stomach multiple times. “But _why?_ I don’t fucking understand why they’re just randomly firing me. I haven’t done anything wrong!”

“Mr. Winchester, I’m afraid you’re causing a scene and I have no further answers for you. The family wishes you well in all further career pursuits.”

As the man turned to walk away, Dean called out helplessly. “Damn it, is Bo okay or not?!”

His only answer was the sight of a large guy with _Security_ written on his shirt, walking into view and holding a hand out to motion to the door.

Dean stepped back into the warm Los Angeles air outside, his head swimming, tears on his face, and absolutely no fucking idea what he was supposed to do next.


	20. Chapter 20

**Notes for the Chapter:**

> This is short, I know, I'm sorry. It was like pulling teeth to get this much done. I think I'm too excited about the next few parts to focus on the filler. LMAO

_Toddler Tip: Tried to do something nice by stirring her coffee and now she’s mad. Is it because I used her iPhone?_

\---

Castiel had never been so scared in his life. He woke up in the middle of the night to the sound of Boston screaming and ran into his son’s room to see him sitting up in bed, covered in sick and clenching his stomach as he cried.

The panic set in immediately, and he he yelled for Gabby. As he circled the bed, he saw a purple stain on the floor and the half empty bottle of baby Tylenol laying there. _Shit._ “Boston—Bo, did you drink this?”

“Hurts,” the child managed.

When Gabby got to the doorway, Castiel looked up. “Call for an ambulance. He got into the ibuprofen.”

\---

Sitting in the waiting room of the ICU, Castiel held his head in his hands and tried to relax. They had finally gotten the levels of ibuprofen in Boston’s system down enough so that he wouldn’t have permanent liver damage, and he was now resting in a private room. Gabby was in there with him, and Castiel wanted to be in there as well—but his head and heart were hurting.

In the panic of Bo’s rushed trip to the hospital, Castiel had tried to find Dean in his bedroom—only to realize that the room was empty. Dean’s car was still out front, but Billy’s was gone and it slowly sank in that Dean had spent the night out with Billy. As he tried repeatedly to call Dean, he garnered no response and eventually Gabby saw what he was doing and scoffed at the actions. Billy wasn’t answering his phone either.

_”Cas,”_ she had said, _”This all happened because of Dean. The medicine being left within Bo’s reach? I haven’t given Boston medicine for anything in weeks, so unless you got the Tylenol down, it had to have been Dean. I’m sure he was in a rush to spend time with my brother and got careless.”_

She continued to tell him that he needed to take a step back, for Bo’s sake. Because she had gone ahead and contacted a lawyer to draft papers for Dean’s termination. According to Gabby, Dean was lucky she wasn’t suing him for child neglect.

The problem was, Castiel had watched Dean with Boston enough to know that Dean would never risk Bo’s health just because he was in a rush. He had Bo on a strict schedule, made sure he ate almost every bite of his food, and always kept him nearby when they left the house on errands. Even inside the house Dean was always vigilant, arranging to fold laundry or prepare food so he could still see Bo wherever he was playing. So Castiel just couldn’t figure out how something as important as putting away medicine would suddenly slip Dean’s mind. 

There was no way, but how did he prove it? He couldn’t. Not without talking to Dean and personally getting his side of the story—and it seemed like Gabby was set on making that impossible. 

When Billy stepped into the waiting room, looking equal parts panicked and lost, Castiel felt the tug on his heart once more. Dean should be there with him. He probably _was_ there… somewhere in the hospital wondering what was going on and if Bo was even okay. 

“Cas, thank God! Where’s Bo? Is he okay?” Billy looked around the deserted waiting room and back out into the halls of the ICU. “Dean’s downstairs. They said he wasn’t approved to come up here until you called them.”

_Fuck._ “Bo is doing a lot better, thank God. He swallowed too much Tylenol, but thankfully we got him here in time. They were able to flush it out before he had any permanent damage.”

“Shit, man,” Billy whispered, collapsing into one of the chairs. “How did he get the Tylenol?”

Castiel ran a weary hand through his hair. “Gabby thinks Dean left it out by accident.”

\---

Dean had half of his stuff packed when his cellphone rang from his pocket. He wanted to ignore the noise and keep on brooding as he packed his things and worried about Boston, but the thought that it might be Castiel made him check his phone. _Billy._ It wasn’t Castiel, but at least he could get answers about Bo’s health.

“Hey,” he answered, continuing his movements. The guard standing downstairs had made it clear that Dean was on a schedule.

“Dean. Hey. I, uh… I’m sorry, for whatever happened.”

Dean choked back tears. He had promised himself he wouldn’t cry until Los Angeles was in his rearview mirror. “How is Bo? What happened?”

“He got into some Tylenol and drank too much. They’ve got it out of his system now.” Billy only waited a moment before continuing. “Gabby is blaming you. That’s why she sent her lawyer to deal with things. I don’t fucking know how she can blame you, when you were fucking amazing with Bo, but she is.”

Well, that certainly explained a lot. He thought back to the last time he had given Boston medicine. If he remembered correctly, it was before they even went to New York. But he couldn’t prove that, and it was pointless to try and fight something that had already happened. “It’s fine, Billy. I just… I just needed to know that he was okay.”

“Dean, it’s not _fine._ My sister is using you as a scapegoat when all you ever did was love her child more than she does. It pisses me off so bad, but I’ve talked to Cas and he says there isn’t anything that can be done.”

That hurt. Probably more than anything else. Castiel wasn’t even trying to stand up and fight for him? “I’ll be alright. They sent me to the house with a guard to get my stuff. I’m working on that now.”

Billy let out a frustrated huff of breath into the phone. “Fuck, Dean. I feel so bad. Where will you go now? What are you gonna do? I could maybe hook you up with a couple of guys looking for roommates?”

“No, thanks.” The thought of staying in Los Angeles made his stomach churn. “As soon as I’m packed, I’m heading home. This whole L.A. lifestyle is not for me. I miss my mom and brother and it will be nice to be back in Kansas for a bit.”

Only part of that was true. He did miss his mom and Sam, but he did not want to go back to the one-horse town that he called home—where everyone knew his name and would know that he tried to make it big and failed miserably.

“Well, if you ever need anything, let me know, okay? Keep my number handy. I’ll update you about things as I get the chance.”

It was a nice thought and good offer, but Dean knew that the only way he would survive would be if he didn’t continue to hear about Castiel and Boston—the two men that had stolen his heart in Los Angeles. 

“Please don’t, Billy. I just… I think it’d be best if I put this all behind me.”


	21. Chapter 21

_Toddler Tip: We have waffles but no syrup. I can’t live like this._

\--- Six Months Later ---

The glamour of Hollywood faded into the fields of Kansas like storm clouds dissipating over a desert. Left in the wake of movie scripts on kitchen tables and week long trips to high-rise New York buildings, was a soul washed out with mud and a mind trying to break free from darkness. Dean was different, Kansas was different, and life was… _different._

His family welcomed him home with open arms, but that didn’t mean he ran to them without reluctance. Beneath the shame of being a failure was the reality of being alone, ripped from the family that he had so happily fallen in love with. He missed Boston and Castiel like they were a lost limb severed without warning. Because in the long run, that’s how things played out. He didn’t even get a chance to say goodbye.

Sitting in his childhood bedroom, in the two story farmhouse that they had lived in since his father died, Dean stared at the picture on his computer screen and felt empty. He was supposed to be studying for his structural engineering class, but had easily gotten distracted by the photo that had been taken when he went to see the Statue of Liberty with Castiel and Boston. They looked so happy.

“Dean?”

He shut the laptop in a rush and looked up at his brother standing in the doorway. “Yeah?”

“Mom asked if you could help with dinner. I would, but I have to finish my science project that’s due tomorrow morning.”

Shoving the computer to the other side of his bed, he stretched for a moment before standing up. “That’s fine, Sammy. Go finish your homework.”

Downstairs in the kitchen, Mary was in the midst of checking on a pork roast in the oven when Dean stepped into the space. It was much smaller than the Novak’s kitchen, but his mother kept it obsessively clean and well organized. Apparently Dean got his OCD from her.

“Sammy said you needed my help?”

Her blonde hair tied up in a messy ponytail, Mary Winchester looked as beautiful as ever right there in her element. She smiled at him. “I mainly just wanted company. And Sammy is killing me with all of his science babble.”

She shoved a cutting board and carrots towards him, and he grabbed a knife and began chopping without even needing to be asked. “I know more about cells and atoms from Sam then I ever learned in high school.”

“He’s overzealous,” she mused, fluttering around the kitchen like a bird. Her moves were graceful, always with purpose, but she didn’t often remain still for long. “How are your classes going? You know, laptops are portable. This house is quiet enough that you could study downstairs sometimes.”

He had received the same speech five times since the fall semester had begun a few weeks back. The truth was, he was struggling. The depression still had a very real hold over his emotions. “I know, Mom,” he answered. Just like he always did.

“Oh! Town gossip.” She moved on, leaving the touchy subjects behind her. “The Jenkins farm finally sold. Looks like we’ll have new neighbors soon. And Rosette down at the salon was asking about you again. She wants to know if you’re going with anyone to the fair this weekend.”

Yet another thing his mother had been nagging him about. Six months was apparently the designated mourning time for a relationship that wasn’t even a relationship. He didn’t want to date _Rosette_ the girl who used to sit behind him in math class and cheat off his papers. Or _Paula_ , whom he went to the DQ with _once_ for milkshakes and suddenly was destined to marry. He didn’t want _any_ of the girls in Smalltown, Kansas. He wanted a film and TV writer that lived in Burbank and had piercing blue eyes and the best fucking cock in the lower 48.

“I promised Sammy that I would drive him and his girlfriend to the fair. I really don’t want to be set up on any dates, Mom.”

Mary shrugged off his reply and began to rant about the local market and how she had asked the manager five times to order a different variety of local fruit because the stuff he was getting was ‘pure shit and couldn’t make a pie if it tried.’

\--- 

The county fair was a cesspool for the weird. Dean followed his kid brother around for all of ten minutes before he was shooed away for ruining the mood and cramping Sam’s style. That, of course, left him wandering around the fair like a lost puppy. Which left him wide open to get trapped by someone like Rosette. It was almost like she was wandering around looking for prey.

When she spotted him, he panicked, looking around and trying to find a quick out but it was pointless. She was already there and pestering him to go on rides with her. 

He suffered through an hour of it, before he made an escape while Rosette went to the restroom. Unfortunately, there weren’t many places to hide and it wasn’t like he could just leave without Sam and his date. 

Dean wound up sitting down in the grass behind the Funhouse, pulling his phone from his pocket and for the millionth time in six months - contemplating calling Castiel. 

“Who are we hiding from?” a voice questioned. 

Looking to the space next to him, Dean watched as Katie Leboux sat down in the grass. “Katie!” He couldn’t believe she was there, and for a moment he was rendered speechless. After their first time together, they had shared only brief glances and soft ‘hello’s in passing at their high school. The girl who’s virginity he took, was nothing like the woman that sat before him. Her chocolate colored hair was in soft curls ending right against her shoulders, and her happy amber eyes sparkled with mischief.

“Hello, Dean. Long time no see. I saw you being drug along behind Posey Rosey and thought you might need an escape. Before I could get there, though, you had already found your own.”

“God, Katie, she’s just as bad as she was in high school.” He shuddered at the thought of Rosette. “She smells like my grandma’s house, how is that possible? Like cod liver oil and moth balls.”

Katie laughed, her head tipping back and her hair sweeping over her shoulders. “She works at the old folks’ home out on the highway.”

“That explains it. Sort of.”

“So how has life been? I heard you moved out west and got away…”

Dean had avoided talking about Los Angeles with everyone, including Sam, who knew the most about the situation. It just felt like if he discussed what had happened, that would make it real. But there was something about Katie—maybe it was the connection she had to his days with Castiel that she wasn’t even aware of, or maybe he was just ready to talk. Whatever the case was, Dean found it easy, sitting there in the grass at the county fair, to tell Katie everything that had happened to him during his three months in California.

\--- 

A week later, Dean packed his laptop into his backpack along with a change of clothes— _just in case_ —and made his way downstairs and into the kitchen. He leaned down next to where his mother sat at the kitchen table and kissed her cheek. “I’m heading out. I’ll text you and let you know if I’m not going to be home tonight.”

Mary looked up at him, shock on her face. “Excuse me, young man? Where would you be going that required you stay out all night?”

“Katie and I are going to have a study session and she’s making me dinner.” He smiled and winked at his mother. “All night studying might commence.”

She slapped his arm and laughed. “You are not fooling anyone, Dean Winchester. But I will let you get away with it _this time_ just because it’s nice to see that smile on your face again.”

“Love you, Mom,” he replied, making his way to the front door. 

“You better have condoms!” Mary called out after him. “I’m not ready to be a grandmother!”

Katie lived five miles across town, in an apartment that was paid for thanks to an inheritance from her father’s estate when he died. It wasn’t the nicest place in town, but it was definitely not cheap either. When he knocked on her door, she answered wearing a tank top and jean shorts beneath a bright pink apron. She had an oven mitt on one hand and grinned at the sight of him. “Come in! I was just about to pull the pie out of the oven for later.”

He stepped inside and kicked his shoes off after closing the door behind him. “A woman after my own heart.”

She poked his nose with the oven mitt and laughed. “I know you well, Dean. I remember you dragging me all over town on our first date and letting me try a bite of every good slice of pie this place has to offer.”

“That was one of my best date efforts.”

“I can believe it.” She went into the small kitchen area and pulled a golden brown Dutch apple pie from the oven. After she had placed it on a cooling rack, she turned back to Dean and winked. “Tonight will be one of my best date efforts.”

And just like that… Dean found himself dating Katie Leboux, the girl he gave his virginity to.


	22. Chapter 22

_Toddler Tip: A fun alternative to sleeping is crying._

\--- One Month Later ---

Every time a knock sounded at the front door, Dean’s imagination went a little wild. Since it was only in his mind and no one else would ever know, he let the fantasies play out. He could picture opening the door and Castiel standing there with Bo next to him and they would hug him like they hadn’t seen him in months—because they _hadn’t_ —and Dean would hug them back and tell them how much he loved them.

They would step inside and Dean would introduce them to his family. His mother would instantly dote on Boston like she was the grandma she feared actually becoming, and Sam would ask Castiel questions about movies that Castiel would laugh about. They would have dinner and then his mom would break out old family photo albums and show off the pictures of Dean as a naked pudgy baby. 

It would be perfection in a moment.

Castiel and Boston were never at the door.

“Hey Katie.” He stepped aside to allow her room to enter. The sun had just set over the plains and his mom and Sam were gone into town to get a pizza for dinner.

Katie leaned up on tip-toes and kissed Dean quickly with a smile. “Hey, hot stuff. I was out in this neck of the woods and thought I’d stop by and check on you.”

Dean rolled his eyes. “You just happened to be two miles out on the wrong side of town…”

Shrugging, Katie moved into the dining room area and sat down at the table across from where Dean’s books were spread out. “My mom sold the Jenkins place next door. The owner is coming into town tomorrow and she wanted some flowers to be on the kitchen counter when they arrived, so she asked me to bring them out.”

_The Jenkins farm._ Dean thought once more about the place and his _other_ daydream. That Castiel had bought the farmhouse in order to live next to Dean’s family and establish their relationship further. It was crazy, though—Castiel didn’t even know which town Dean was from. But it didn’t hurt to ask… “Hey, did the new owner’s last name happen to be Novak?”

Katie’s brow furrowed in contemplation, and she waited a minute before shaking her head. “No, that doesn’t sound familiar. Why?”

“No reason,” Dean whispered.

She watched him closely, obviously gauging his reaction as he sat back down in front of his work. “I’m fairly certain she said the buyer was a lawyer from Chicago.” When his face fell a bit, she continued, “I know you still wish he would show up and sweep you off your feet…”

“Pfft.” Dean forced a smile and a wink, masking his pain as best he could. “I’m not a girl, Katie. You should know that by now.”

There was a commotion at the door as Mary and Sam stumbled in carrying pizzas and soda and arguing about the best John Wayne movie. Mary spotted Katie sitting in the kitchen and smiled. “Katie, dear, it’s good to see you again! Dean didn’t say we’d be having company—it’s a good thing I bought extra.”

“Oh I couldn’t possibly impose, I just stopped by to check on Dean—”

“Nonsense, we love having you here. It keeps Dean on his best behavior.” Mary stepped up behind Dean, her hands free now that she had placed the food on the kitchen counter. She ruffled his hair like she used to when he was little. “Maybe later we can break out the photo albums.”

Beneath his forced smile, Dean felt the pain of his mother’s words like a dagger to the heart. 

It should have been Castiel at the door.

\---

In the podunk town that he called home, there weren’t many job opportunities. It took Dean four months to find something and, considering it was a minimum wage gig at the local supermarket as a cashier, he didn’t brag about the job to anyone. Being so front and center in such a small town meant that he saw almost everyone pass through his checkout line at least once.

He knew things about the town that he never wanted to know. Stupid shit like the fact that Mrs. Davies liked to have young strapping men in her bed and bought an awful lot of XXL condoms and grape flavored lube. And creepy Mr. Haywood stocked up on bags of candy in bulk, leaving Dean fearful for the neighborhood children. 

The Smiths were having their sixth baby in February. The Johnsons were getting a divorce because Mr. Johnson slept with Susie Roland, their daughter’s best friend. And… whoever bought the Jenkins farm had gone all out when they ordered furnishings for the place. They had also called in a contractor to put in a swimming pool in the backyard. 

Dean’s curiosity over the lawyer from Chicago that would be their new next door neighbor had long since waned. If it wasn’t Castiel buying the place to surprise him, Dean really didn’t fucking care. 

He watched the clock turn over to five p.m. and happily said goodbye to his workmates before walking to the back and clocking out for the day. His leather jacket in hand, he walked back out to the parking lot and smiled at the sight in front of him. Leaning against the hood of his car, Katie stood wearing a short black skirt and sparkling blue top. He moved to her on auto-pilot, pressing his body against hers and ducking down to kiss her. 

When the kiss broke, she stared up at him with those sparkling gold eyes. “I just got done with an interview and thought you might need a massage after your day.” 

“You have no idea how nice that sounds,” Dean whispered, kissing down to her neck and letting his fingers brush beneath the back of her top. “Especially if it’s going to be a naked massage.”

“Only the best for you, babe.”

He unlocked the passenger door and held it open so that Katie could climb inside.

After he shut the door, Dean looked over the top of the car and for a second he thought he saw familiar dark brown hair turning and walking away. “Cas?” he whispered, aloud, but a truck pulled into the parking lot, blocking his view. He had been in similar situations enough times over the last ten months to know that he couldn’t follow. It was always a setback in his emotions. 

Walking around the car, he plastered on his fakest smile and climbed behind the wheel. “I might need a shower before I let you massage me—the store was stupidly hot today.”

“Well I know you think shower sex is complicated, but I’m sure mine is large enough to allow for playtime—”

\---

It was the moments when Katie was laid out in bed before him, all soft flesh and delicious curves, that Dean missed Castiel the most. It really worked to ruin a guy’s self-perception of his own sexuality when sex with a woman turned into dreams about a man. Dean couldn’t help it though. He would give anything to trade Katie’s breasts for the hard lines of Castiel’s muscles. To go down on his partner and taste the salty bitterness of precome instead of the juicy slick dripping from a pussy.

He wanted to hear Castiel’s voice ringing in his ears, moans and cut off gasps of ‘more’ and ‘Dean’ and _’so fucking good.’_

He was doing more damage than good by pretending that he could be with Katie and things could be normal. She understood—she told him repeatedly that she did—that she could wait however long it took for him to move on and love her like he loved Castiel.

But he could still see the glimmer of sorrow in her eyes when he drifted from his mind and came with Castiel’s name on his lips. 

When she finally fell asleep, Dean placed a note on the table next to her bed and walked out of her apartment like the coward that he was. A million _’I’m sorry’_ s wouldn’t make up for stringing her along while he went through the pile of emotional bullshit in his mind.

He drove down Main street on his way home, and for a moment he could pretend that the soft streetlights were as bright as the lights of Hollywood. He could imagine taking the shortcut on Maple street and arriving at the Novak home just a few minutes earlier than usual. Walking inside and hearing Boston scream his name and come running, tackling his legs in the biggest hug that the three-year-old could manage.

Dean had tears on his face as he parked the car in his mother’s driveway. He laid his head forward on the steering wheel and cried—unable to continue fighting it.

Twenty minutes later, he climbed from the car and walked to the porch, thankful that his mother and brother would be asleep by that time. 

He stopped short, though, frozen halfway up the sidewalk when he saw a form sitting on the top step. A head of dark hair raised up and suddenly familiar blue eyes were staring at him.

Dean wasn’t sure if he should scream out in anger or cry tears of joy. Hug the man or slap him silly…

“Hello Dean,” Castiel said calmly.


	23. Chapter 23

**Notes for the Chapter:**

> All screaming can be directed [here.](http://archofimagine.tumblr.com/ask)
> 
> *whispers* we're getting so close to the end that it's _scary_...

_~~Toddler Tip:~~ Just checked in @ Time Out (w/ 0 other people)_

\---

Beneath the shock and excitement at seeing Castiel again, Dean felt anger. Despite the fact that he had literally spent _months_ wanting Cas to show up on his doorstep, the actual reality of him being there was frustrating. _Why_ was he _there_? “Why are you here?”

Castiel didn’t seem at all phased by the anger in Dean’s voice. He simply stood, brushing off his slacks and moving the few steps to where Dean remained frozen. After a long moment of staring Castiel closed the distance between them and wrapped his arms around Dean. The anger momentarily seeped away as Dean reacted on instinct and relaxed against Castiel. It felt good… no, it felt _amazing._ But that didn’t mean it was right.

When Castiel finally pulled back, he had a nervous smile on his face. “We need to talk. Mind going for a walk?”

Dean’s eyes flicked up to the house behind Castiel and he knew that even if it looked dark and seemed like everyone was sleeping, that wouldn’t keep his family from eavesdropping if they woke up and heard voices. “Sure.” He turned and waved for Castiel to lead the way. When they started walking slowly down the driveway, Dean continued to nervously wait for answers to questions he was too afraid to ask.

“I want to start by saying that I’m sorry it’s taken me this long to see you. I had a lot of important people making it very clear that the best outcome would result from me keeping the ties severed between us.” Castiel stopped at the edge of the driveway and turned to look at Dean. He held up his left hand and showed Dean that there was no longer a silver band there to glint in the moonlight. “Gabby and I are officially divorced. It took longer than I wanted it to, but it’s done and over with now.”

He stared at the bare finger on Castiel’s hand. He had no idea what to say. He wanted answers and he wanted more than anything to see Boston again, but that didn’t mean he had wanted Castiel’s marriage to end. Even if he could admit to himself that he was in love with the man, he would never force his way between Castiel and Gabby.

“I know,” Castiel continued, practically reading Dean’s thoughts, “that this isn’t what you wanted. Every time you pushed me away I could see it in your eyes that you were giving up your own desires for the greater good. I’ve come to understand that… that’s just who you are, Dean.”

Dean turned, looking back at the aged farmhouse that he had grown up in and remembering the way his mother had struggled after his father died. Life in a single parent family had never been easy or normal. And he wouldn’t wish a childhood like that on anyone—let alone the little boy that had stolen his heart. 

“Bo deserves better than that,” Dean whispered, still staring at the house.

“Just because his parents are no longer married doesn’t mean Boston will lose out on anything in his life. It’s my hope that he’ll gain more from this experience than he’ll lose.” After a brief pause, Castiel’s voice broke as he continued. “It was Gabby, Dean. Boston got into the Tylenol because of Gabby. I had no clue but, apparently, the night before she gave him some so that he would fall asleep faster. She thought he would be down through the night, so she left the bottle beside his bed instead of putting it away.” 

“ _Fuck._ ” Dean felt frustration and anger boiling up inside of him. “She could have killed him! How could she be so fucking stupid?”

“She was selfish. Once Boston was awake and out of the hospital he mentioned something about thinking it was okay to drink the purple stuff because mommy gave it to him. That’s when I knew that something was wrong and I needed to find a way out.” Castiel shook his head. “Once we were in front of our lawyers, she finally broke and started screaming about how she never wanted the pressure of motherhood. She said I forced her into being a parent so that she wouldn’t leave me.”

Dean took a deep breath. He wanted to yell in anger over how much he hated Gabby for ruining everything with her selfishness, but he knew that she didn’t deserve the focus for another moment. As Castiel continued walking, Dean followed a step behind. “How is Bo?” Before Castiel could answer, a thought dawned on Dean and he followed up his question with another. “And the baby?”

Crossing his arms over his chest, Castiel grinned. “Boston is doing well. He recovered quickly and was only in the hospital for a few days. The worst part was wondering where you were. I… I can’t tell you how many times he woke up crying for you. I didn’t have any answers for him other than that he would see you soon. Eventually, once Gabby moved out, I just let him sleep in my bed so that when he woke up crying, I could hold him and talk about how much I loved you too.” 

As Castiel continued walking, Dean stopped short. He covered his face with his hands and knew it was pointless to hide his emotions. If only Bo could know that the feelings were always mutual. That at the same time, Dean was waking up wanting to hold and talk to Boston.

A few seconds later, his hands were gently pulled away and Castiel was reaching up to brush his tears away. “This is why I know that Boston will not be missing out on anything, just because his parents are divorced. Because he has the love of the best man I know. _You._ ”

Surging forward, Dean curled his hand over Castiel’s neck and up through his hair as he did something he’d been thinking about doing for ten long months… and softly but surely kissed the other man.

Castiel seemed reluctant to pull away, but he obviously had more to say. Even so, he placed one more chaste kiss on Dean’s lips, before grabbing his right hand and turning to continue walking down the deserted street. “Gabby gave up custody once the baby was born. It was something I thought I’d have to fight harder for, but with the threat of information being leaked about her poisoning her own child, she gladly took a step back. Last I heard, she’s already brought Paul to Los Angeles.”

“Of course she has,” Dean mumbled. He paid little attention to where they were walking, more curious about Castiel and the kids. “Are you handling everything on your own then? Is that why you’re here? To hire me back as a nanny?” He frowned at the thought. There was no way he could go back to being in a position where Boston and Castiel could so easily be ripped away from him. 

“Actually no.” The other man stopped walking at the edge of a driveway and smiled at Dean. “I don’t need a nanny. The kids need parents, not a dad and a nanny. So if you think that’s what I’m offering, Dean, then I’m afraid we might be on the wrong page.”

He frowned. “Parents?” After everything that had transpired over the last few minutes, was Castiel seriously discussing his need to find a mother for Boston and the baby?

“Yes.” The smile grew until Dean could see the hint of a sparkle in Castiel’s eyes. “I’ve discussed this thoroughly with Boston. He said it wouldn’t be right to call you Dean, but that ‘papa’ also didn’t fit. So at this point, I’m sorry to say, we’re stuck on calling you ‘Super Daddy Dean, hero of all the lands.’ It’s a bit of a mouth full, but I’m sure you’ll get used to it.”

“ _Me?_ ” Dean croaked, because there was no way he hadn’t fallen into a dream sequence at some point. “You want me?”

“More than you could ever imagine. Dean—you were the light shining at the end of the tunnel that I never thought I would see. The answer to all of my prayers and hopes that my family could finally be happy. And after everything, Dean, you were always much more than just the nanny.”

He looked around, feeling equal parts overwhelmed and speechless. He didn’t know how to accept the offer. It was the promise of a family of his own, and fuck that was scary, but there was no way he could say no to Boston and Castiel. 

Dean’s eyes caught sight of a glow at the end of the driveway, and it took a moment for him to realize where he stood. “You bought the Jenkins farm, didn’t you?”

“Actually, my lawyer did. I didn’t want to sign my name on the papers until you were there to sign on the line next to it. Because I can’t offer you marriage—not yet anyway—but I can offer you a shared home, two beautiful kids, and a partner that loves you.”

“Tomorrow you’re going to tell me how you figured out where I live,” Dean whispered with a soft laugh.

“Gladly.”

“Castiel?”

“Yes, Dean?”

He would never tire of hearing Castiel say his name. He looked to the man beside him and grinned. “What’s our baby’s name?”

Castiel squeezed Dean’s hand. “Brooklyn. Would you like to meet her?”


	24. Chapter 24

**Notes for the Chapter:**

> FYI: I'm posting a big project tomorrow for the Team Free Will Big Bang called 'Sinners Like Me' - I hope you all give it a chance and check it out!
> 
> Also, the last line of this story is by far one of my most favorite lines to ever write. I think it's absolutely poetic. Enjoy.
> 
> (BottomDean/TopCas below)

_~~Toddler~~ Newborn Tip: Gassy smiles are an appropriate reaction to new relatives. _

\---

As they walked towards the house, Castiel clutched Dean’s hand like he was worried Dean would disappear. There was no way that was going to happen now—it would take the end of the world to make Dean leave before he saw Bo.

When they made it to the front porch, Castiel stopped and turned to face him. “Just so you know, things have not been the same without you around. So, don’t be alarmed when you walk in here and Boston comes running like he’s hyped up on pure sugar.”

“ _What?_ ” Dean looked at Castiel like he was insane. “It’s after midnight!”

At Dean’s loud outburst, the porch light flicked on and suddenly the front door was thrown open. A rush of blonde hair and small body came flying out of the house like it was on fire.

“Deannnn!” Boston shouted, wrapping around Dean’s legs and hugging him tight. 

Reaching down, Dean picked the boy up and hugged him close, unashamed of the fact that tears were sliding down his face and landing on Bo’s pajama shirt. “Oh Bo, I’ve missed you so much.” Boston clung to him, and based on the small shivers his body was making, Dean could guess that he was also crying. “I’m never leaving you again,” he whispered. “I promise.”

It took a few long minutes, but finally Boston raised his head and peered at Dean with red swollen eyes. “I missed you,” he said in his sweet little voice.

“I know buddy, me too.”

“Daddy can’t do space cheese, Dean. He just can’t.”

Dean kissed the boy’s forehead and smiled. “Well then—I know what we’re having for lunch tomorrow.” Dean looked at the boy clearly for the first time. Had he ever _grown._ It hurt Dean that he had been away long enough for the time to make such a difference. But, he reasoned, they grew like weeds at that age. Sammy sure had.

“Guess what!” Boston’s emotions changed in an instant and suddenly he had a grin spread out over his face.

Dean shook himself out of his reverie, turning his attention fully on the boy clinging to him. “What?!”

“I have a sister now! Wanna see?” He wiggled free from Dean’s arms, but clung to his hand the way Castiel had, as he lead Dean into the house. “Her name’s Brooke. She likes to scream,” he said plainly.

Dean had been inside the Jenkins home only once in his lifetime and back then, in the wake of Mrs. Jenkins’ death, the place had felt like little more than a mortuary. Now, in the middle of the night, it was like a party. Right in the middle of the sofa in the living room, Billy sat with a cheerful smile on his face and waved the instant he saw Dean. Dean waved back, but quickly followed Billy’s gaze to Castiel. He knelt to the edge of a colourful quilt that was laid out in front of the sofa, and was littered with stuffed animals and other baby paraphernalia. He scooped up the baby into his arms carefully, stood, and brought her over to Dean.

She had the chubbiest cheeks Dean had ever seen on a baby, and he laughed softly as she was placed in his arms and stared up at him with bright blue eyes. “Hello Brooklyn. It’s nice to finally meet you.”

The baby smiled, showing off perfectly shaped dimples. 

It was official… Dean Winchester was in love.

\---

It was nearing two in the morning by the time the kids finally went to sleep—Boston in his room and Brooklyn still in Dean’s arms. He found he just couldn’t let her go. Dean texted his mother at some point to inform her that he wouldn’t be home until later in the day—and to expect guests for dinner. Then he happily carried Brooklyn up the stairs to the nursery and laid her gently in her crib. As he watched her sleeping, he contemplated the fact that Castiel had offered to let him play a permanent role in Brooklyn and Boston’s lives. To be their second father.

The thought alone was intense, but not any more so than the idea that if he declined the offer, he wouldn’t ever see the kids again. Even if Castiel wanted to stay in town it would just be too confusing for the children to live so close to Dean but not actually be a part of his life. It was all a lot to accept—and Mary Winchester was definitely going to have his hide over the whole thing —but he couldn’t lose them. Not again. They were his family just as much as his mom and Sam were.

“Come on,” Castiel whispered from the doorway. “One more bedroom to see.”

Dean clutched the other man’s hand and followed down the hall to the last room. When Castiel opened the door, Dean wasn’t sure what he was expecting, but the empty space—void of anything but a king sized bed and a wooden dresser—was not it. “Nice, uh, interior decorating.”

Castiel slapped at Dean’s ass and shoved him into the bedroom so he could shut the door. “Forgive me for thinking you might want an opinion.”

“Me?” Dean shook his head and laughed at the look on Castiel’s face. “I thought I was just here for the kids, not decorating advice.”

In the moment it took Dean to blink, Castiel rushed at him and tackled him onto the bed. He managed a surprised ‘oh my God!’ before he was pinned down on the plain blue bedspread.

Castiel laughed, dipping his head to kiss Dean’s nose. “I would like your advice on every matter, from now on.”

“Sure.” Dean reached up, brushing his hand beneath the back of Castiel’s shirt. “Might I make a suggestion for the first topic?”

Letting his kisses trace the line of freckles on Dean’s cheekbone, he whispered gently, “Which would be…?”

“I’ve spent seven months thinking about something very important.” He shifted his hips up, letting Castiel feel the way his cock was beginning to harden in his jeans. “You promised me once, that when I was ready you would show me what it feels like to be fucked properly.”

Castiel groaned, his head falling to Dean’s shoulder. “And?”

“And I’ve spent seven fucking months thinking about how ready I am.” It had to be the cheesiest line that Dean had ever spoken, but that didn’t make it any less true. He propped his head up and watched in amusement as Castiel suddenly pulled away in a rush and stood up. 

“Shit,” he said, looking around the room for a moment. It was like he had lost his head. “I know I have supplies stashed somewhere.” He pointed at Dean. “Don’t move.” He walked two steps towards the ensuite before turning back to Dean and pointing again. “On second thought, go ahead and move enough to get rid of those damn clothes.”

Dean happily obliged the request, throwing his clothes in every which direction as he stripped completely. He then moved further back on the bed, trying to get comfortable and look relaxed despite the bugs fluttering around in his stomach.

When Castiel emerged from the bathroom once more, he held up a bottle of lube and a condom wrapper triumphantly. “I knew it!”

“A plus. Now make sure the door is locked so that the little man doesn’t walk in on us.”

“Smart.” Castiel nodded, going to the door and making sure it was securely locked, before moving back to Dean. He tossed the supplies onto the extra space of the bed and quickly tore off his own clothes without much regard to their condition. “Just so you know, I’m _excited_ because I get to be with you again. I would be just as excited if you wanted to top. This isn’t a power play—”

Dean laughed, sitting up and reaching out for Castiel. “Come here, you big goof.”

Castiel settled onto the bed beside Dean and happily returned Dean’s persistent kisses. Since they were both obviously nervous, Dean had no problem enjoying the extended make out session, even if his cock kept nudging at Castiel and demanding attention. 

After a few minutes, Castiel pulled Dean’s left leg over his own body, and Dean heard the soft click of the lube being opened. He tensed, in reflex, but Castiel brushed his free hand through Dean’s hair and leaned down to kiss his neck.

“Just relax. We’re in no rush here, right?” Castiel waited until Dean nodded, before slowly brushing a slicked up finger along Dean’s rim. 

He wouldn’t go nuts and say that it felt amazing—because frankly it felt _weird_ —but it wasn’t a bad sensation, and after just a few moments, Dean found himself pressing back against the touch. “Please.”

“Of course, Dean,” Castiel whispered. He moved slowly, expertly, using first one and then two fingers to loosen Dean and brush the hint of a touch over his prostate.

It took barely any time before Dean was a figurative puddle of desire. “Another. More.”

Castiel gently added another finger, before letting his voice drift against Dean’s ear, “You know, with the perfect amount of stimulation, it’s possible to come from having your prostate massaged. Without even touching your cock.”

Dean shuddered at the thought, feeling his dick jumping in response. He could definitely see how that was true, because he was leaking precome like crazy and felt like the edge was _rightthere_ even without having a hand on his dick. But that wasn’t what he wanted. Not at that moment. “Next time,” he managed. 

“Deal.” Castiel waited a few moments longer, making sure that Dean was as ready as possible, before he placed a spattering of kisses on Dean’s shoulder. “I think you’re ready, Dean.”

“Mmm. Please.”

Pulling away, Castiel threw his hand out across the bed in search of the bottle of lube and condom. He wrapped the latex over his own swollen cock and groaned. “Roll onto your back.” He kissed the side of Dean’s lips. “I want to see your eyes.”

Dean did as instructed, watching Castiel settle between his legs and lift his hips to place a pillow beneath his lower back. He wrapped his legs around Castiel’s waist and took deep calming breaths as he felt the blunt head of the other man’s cock breaching his entrance. 

The pace was slow and controlled, and when Castiel was finally buried deep inside he leaned down to kiss Dean.

It wasn’t until they were both ready and Castiel began to move that Dean decided he could actually enjoy the feeling. It was a new experience and, though he might not sign up for it every time, he could definitely see letting it happen again more than once in the future.

And watching Castiel’s face, watching the love that registered in those shining blue eyes, was the feeling that nudged Dean back to the edge. Castiel knew immediately that he was close, and wrapped his hand around Dean’s cock to stroke firmly until he was coming all over his own stomach. 

Castiel lasted only a moment longer, before the tight sensation of Dean’s body flexing around him was enough to push him past the brink of his own orgasm. He collapsed forward over Dean and let out an exhausted huff of breath. 

“I love you so fucking much,” was spoken gently into the empty room. And it was a promise of forever, no matter who spoke the words.


	25. Chapter 25

_~~Toddler~~ Newborn Tip: Seriously though - who are these people?_

\---

Dean woke up the next morning and smiled at the sight of Castiel snoring softly on the other side of the bed. They had been up late enough the night before that he didn’t bother waking the other man. Instead, he climbed out of bed and quietly searched through the lone dresser for some of Castiel’s clothes that would fit. He didn’t much feel like wearing what he had the night before.

Settling on a pair of gray sweatpants and a worn out t-shirt that looked to be from Castiel’s college days, Dean got dressed and left the bedroom. He checked both of the kids’ rooms, but they were empty, and from downstairs he could hear the sound of Billy talking to someone. 

When he entered the kitchen, he found Boston sitting on a stool at the island and Billy running around like a mad scientist while trying to fix what Dean hoped was pancakes. In a bouncy chair sitting securely on the countertop, Brooke was buckled in and happily shaking a soft rattle toy. Dean smiled, moving up behind Boston and dipping down to kiss the top of the boy’s head. “Good morning.”

On that particular morning, Billy was dressed in red skinny jeans, an atrocious multi-color striped button down, and bright blue suspenders. Dean would never understand how Billy managed to go shopping and never buy _anything_ normal.

“Dean!” Boston spun around on his chair and wrapped his arms around Dean’s waist as best he could. “G’morning.”

“Is Uncle Billy ruining breakfast?” Dean swooped Boston up into his arms, causing the boy to laugh, and then settled onto the same barstool—this time with Bo sitting on his lap. “Because it looks like he’s making a mockery of pancakes.”

Billy looked across the room and stuck his tongue out, waving a dripping spatula in their direction. “Shush, you. I apologize for not being Mr. Mom like the great and powerful Dean-o.”

Dean reached over to the spot where Brooke was on the counter and tickled her toes, causing her to kick out against the feeling and babble around the rattle in her mouth. She was such a beautiful baby. Bright blue eyes and hair the same shade as her father’s. Dean wanted to spend hours holding her, loving her, and spoiling her. After a few moments of being distracted by the baby, he turned back to look at Billy. “Hey, so, I gotta ask—why are you here? What happened with the feud between you and Cas?”

“He needed help. He knew he wanted to get here, and knew that it would be a long process, but he didn’t want to hire anyone to help with the kids. I just wanted to help get them away from… _her._ So I’ve been working on my thesis and trying to do your job.” Billy set a plate down in front of them—Dean would forever wonder how someone could make a _square_ pancake—and moved back across the kitchen. 

On instinct, Dean wrapped his arms around Bo and used a fork to cut up the pancake into small, manageable pieces. He then let Boston take the fork, and looked back up at Billy. “So is it really over? Was it really that easy to get her to say goodbye?”

“I don’t think easy is the proper term. It was a nasty process, but yes… it’s really over.”

“Dean. _Dean._ ” Bo turned, holding his fork with a small bite of syrup drenched pancake on the end. “Bite?”

With a laugh, he leaned forward and grabbed the bite into his mouth. After chewing and swallowing, Dean smiled. “Thank you, Bo.”

\---

Mary Winchester could handle a lot of things. She had single-handedly raised two trouble-making boys while also working hard enough to keep a roof over their heads and food on the table.

She saw them through broken bones, bruises, and cuts. Shattered hearts, lost loves, and that one prom where Dean got drunk and subsequently suspended.

She was a rock, steady and unbreakable.

Until, of course, her oldest son decided to show up on her doorstep with two kids and a boyfriend. 

Dean walked into his childhood home with Brooklyn strapped against his chest in a baby carrier, and Boston clinging to his right hand. Castiel followed them in, weighed down by the diaper bag he was carrying. 

Standing at the entrance to the foyer, Mary held a dish towel in her hands and stared at the sight like she was watching aliens walk through her front door. “Dean?”

“Hey mom.” Dean wasn’t worried at all about her reaction. “I have some people I’d like you to meet.” He waved Boston’s hand in the air wildly, causing the boy to giggle. “This is Boston. The baby is Miss Brooklyn. And the tall weirdo is Castiel Novak.”

Stepping around Dean and the kids, Castiel held his hand out to shake Mary’s. “Nice to meet you, Mrs. Winchester.”

To Mary’s credit, she _didn’t_ faint. Dean watched her force an unsteady smile onto her face as she shook Castiel’s hand. “Come on in. Have a seat in the living room. Dean—can I talk to you in the kitchen?”

“Yeah. I’ll be right there.” He lead Castiel and Boston into the living room, and motioned to the pile of toys in the corner. “Look Bo—you see those? You can play with anything you want, okay? I’ll be right back.” His mother had officially retired from running a daycare, but had a few select children that she watched to help with random bills.

Following Mary’s path into the kitchen, Dean laid his hand gently on Brooklyn’s back and smiled at his mom. “Cas bought the Jenkins place.”

“Why is he here, Dean?” she asked, laying the towel down on the counter. 

Dean waited a moment, the smile falling from his face. He expected his mom to be happy for him, even if she was a little confused. Based on her tone of voice—happy was a long ways off. “Me, Mom. He’s here for me.” She continued to stare at him, obviously waiting for an explanation. “Cas and his wife had an open marriage. He and I had a fling while I was out there. It was… intense. It still is. Once his divorce was finalized, he moved here to be near me.”

“So that instead of paying you for nanny care, he can suddenly get it for free.” Mary shook her head. “Dean—I know what you’re thinking. I know, because I’ve been there too. I had an affair with one of the fathers I used to babysit for. It was amazing, but it wasn’t real. After two months, he asked me to start lowering his rates. Wanted to work out an arrangement, he said.”

Instantly frustrated, Dean shook his head. “Castiel isn’t like that! He’s got money, Mom, he could have easily gotten another nanny. Why would he wait seven months to try and find me? And he did indeed have to find me—it wasn’t like I told him where I grew up.”

“You’re not even gay, Dean. You’ve only ever had girlfriends—and suddenly you want to show up here with a guy and claim to be starting a relationship?”

He sighed. “No, I’m not gay. But that doesn’t mean I can’t have feelings for a man.”

“What about Katie?” Mary frowned. “You two were such a cute couple—and things were going so well!”

He closed his eyes, picturing Katie for a moment. She was on his list of people to call, and he knew that she would understand completely. That was just the type of girl that Katie was. “She knows about everything that happened with Cas. If anyone will understand, it’s Katie. She’ll be excited for me. Just like I wish you would be.”

Mary took a long deep breath, staring down at the counter as she seemed to wage an inner war with herself. After a moment, she looked back up at Dean. “I want to be happy for you, but you’re my son and I’m worried that you’re rushing into a mistake that’s going to get you hurt.”

“Mom—Cas is the reason why I showed up here seven months ago looking so wrecked. Being forced to leave him and Boston _broke my heart_. I won’t lose them again. Even if it makes you unhappy.”

She finally nodded, small smile back in place. “Alright. I will give him a chance. _For you._ ” She stepped forward, holding her arms out. “Now let me hold this baby.”

\---

In contrast to his mother, Sam decided that he loved Castiel immediately. Once he got home from school and introductions were made, Sam began to pester Castiel with questions about writing and Hollywood. Out of nowhere, Sam proclaimed that he had been thinking about becoming a writer and studying English when he went to college.

Dinner was nothing short of an affair. Mary somehow managed to produce a meal for all of them with Brooklyn held against her hip the majority of the time. She was smitten and refused to give the girl up. 

Boston, on the other hand, continued to cling to Dean. Despite having a chair of his own between Dean and Castiel, Boston demanded that he sit on Dean’s lap throughout dinner. When Dean lifted the boy into place, he glanced over to Castiel and received only an amused smile and half shrug in response. 

Once they were done and the table was cleared, Mary and Sam convinced Boston to settle down and watch an old Disney cartoon. With both kids taken care of for the moment, Dean grasped Castiel’s hand and pulled him out the front door. They both sat down on the step where Dean had happened upon Castiel the night before, and pressed close together as they looked out at the clear night around them.

“I give it a week before Boston is calling your mother ‘Grandma’,” Castiel mused, throwing his arm over Dean’s shoulders.

“A week? Three days, tops.” Dean let his head drop onto the other man’s shoulder and took a deep breath. “Cas, this thing between us… it’ll _just_ be us, right?”

Castiel seemed to catch on immediately to what Dean meant. “You know, I’ve come to understand that there is nothing wrong with polyamorous relationships. With the right people, the right love, and proper communication—it’s a perfect solution for some.” He paused, turning to kiss Dean’s forehead gently. “But it’s not for me. I would never be able to share you, Dean, nor would I ever want to force you to share me.”

There was a long pause and the night was filled with the sounds of the crickets and frogs chirping and croaking from the yard.

From inside the house, Dean could just barely make out Boston and Sam laughing. It suddenly dawned on him that for the past three years, he had been dreaming about leaving Kansas and finding the perfect life. The seventeen-year-old version of Dean Winchester would have never believed that ‘perfect’ involved two kids and a relationship with a man. 

But there they were. And suddenly he didn’t need to go looking for everything he wanted in life. 

What was the point, when they had found _him_ right there in Kansas?

“I love you, Cas,” Dean whispered. “Thank you for coming to find me. Thank you for bring Bo and Brooke and giving me the life I never knew I needed.”

\--- **The End** \---

**Notes for the Chapter:**

> There will probably be a sequel chapter popping up for this in the next couple days. Thank you to everyone that has followed along with this story - it has been an amazing experience! I am grateful for every one of you!


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